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Journal articles on the topic 'Acetylene diols'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Juraboev, Fozil Mamasolievich. "SYNTHESIS OF ACETYLENIC DIOLS BASED ON ACETYLENIC ALCOHOLS." Research Focus 1, no. 2 (2022): 17–22. https://doi.org/10.5281/zenodo.7237916.

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<em>This article examines the influence of various factors on the performance of the main product in the synthesis of acetylene diols based on direct condensation of acetylene alcohols with aldehydes and ketones.The influence of factors such as the structure and nature of acetylene alcohols on the yield of acetylenediols, the composition and nature of carbonyl compounds, temperature, catalyst, reaction duration has been studied.</em>

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2

Kienzle, Frank, and Rudolf E. Minder. "Synthese von spiro-substituierten Cyclopentenonen und analogen Verbindungen." CHIMIA 39, no. 4 (1985): 100. https://doi.org/10.2533/chimia.1985.100.

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3

Wang, Guoyong, Jiangxun Dou, Jiaoyan Liu, et al. "Influence of acetylene bond on surface activity of acetylenic diols in aqueous solutions." Colloid and Interface Science Communications 54 (May 2023): 100710. http://dx.doi.org/10.1016/j.colcom.2023.100710.

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4

Konno, Tsutomu, Gen Egashira, Chihiro Kajimoto, Takuto Kataoka, and Shigeyuki Yamada. "Synthesis and Application of Tetrafluoroethylene (CF2CF2)-Containing Acetylene Derivatives." Synthesis 52, no. 13 (2020): 1947–58. http://dx.doi.org/10.1055/s-0039-1691744.

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On treating 1,3,4-tribromo-1,1,2,2-tetrafluorobutane, readily prepared from commercially available 4-bromo-3,3,4,4-tetrafluorobut-1-ene, with 3.3 equivalents of LHMDS at 0 °C in THF, the corresponding lithium acetylide could be prepared quantitatively. The acetylide reacted well with various aldehydes, ketones, or chlorosilanes to give the corresponding acetylene derivatives in high yields. It was also found that various iodoarenes could participate in the cross-coupling reaction with the zinc acetylide, readily prepared from the lithium acetylide and ZnCl2·TMEDA complex, in the presence of Pd

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5

Oparina, Ludmila A., Nikita A. Kolyvanov, Olga A. Tarasova, Alexander I. Albanov, Anatolii P. Tantsyrev, and Boris A. Trofimov. "Nucleophilic Addition of 1,1′-Bis(hydroxymethyl)ferrocene to Alkynes: Synthesis of Ferrocene Diethenyl Ethers." Synthesis 52, no. 02 (2019): 320–26. http://dx.doi.org/10.1055/s-0039-1690295.

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Chemoselective and atom-economical methods for the synthesis of ferrocene diethenyl ethers have been developed via direct base-catalyzed addition of 1,1′-bis(hydroxymethyl)ferrocene to various acetylenes. This ferrocene diol has been shown to be capable of adding to acetylene (KOH/DMSO, 70–80 °C, 1–3 h), propyne (KOH/DMSO, 70 °C, 12 h), phenylethyne (KOH/DMSO, 20–25 °C, 48 h), alkylpropiolates (DABCO, 10 mol%/CH2Cl2, 20–25 °C, 0.5 h), and acylacetylenes (DABCO, 1 mol%/CH2Cl2, 20–25 °C, 0.5 h) to afford the corresponding diethenyl ethers in 73–98% yields.

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6

Friesen, Richard W., та Suzanne Bissada. "Total synthesis of (±)-9-deoxygoniopypyrone. Application of the iodocyclofunctionalization reaction of bold α-allenic alcohol derivatives". Canadian Journal of Chemistry 76, № 1 (1998): 94–101. http://dx.doi.org/10.1139/v97-212.

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The synthesis of ( ±)-9-deoxygoniopypyrone (1) from the α-allenic alcohol 5 is described. Iodocyclofunctionaliztion of the N-tosyl carbamate derivative of 5 using I2 and Ag2CO3 provided, in a highly diastereoselective and regioselective fashion, the vinyl iodo syn-vicinal diol 4. Two routes were explored in order to introduce the third stereogenic centre in the molecule. Reductive deiodination of the vinyl iodide and diastereoselective epoxidation of the derived acetonide14 using mCPBA provided a mixture of epoxides 15 and 16 (2:1) in which the desired threo diastereomer predominated. Alternat

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7

Xu, Yao-Chang, Michel Cantin, and Pierre Deslongchamps. "Stereocontrolled construction of A.B.C.[6.6.6] tricycle via transannular Diels–Alder reaction of 14-membered macrocycle with acetylene as dienophile." Canadian Journal of Chemistry 68, no. 12 (1990): 2137–43. http://dx.doi.org/10.1139/v90-328.

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The syntheses of the acyclic dienynes 14a (cis-trans-acetylene) and 14b (trans-trans-acetylene) are described. The tandem macrocyclization and transannular Diels–Alder reaction of the allylic chloride 14b was conducted in the presence of Cs2CO3 at 85 °C in one-pot to provide tricyclic product 16, with the two hydrogens in ring B being cis. On the other hand, treatment of the allylic chloride 14a under the same conditions afforded 14-membered macrocycle 17, which could be transformed at 250 °C into a similar tricyclic product 18 with the two hydrogens in ring B being trans, along with an intere

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8

Sarmah, Manas M., Debajyoti Bhuyan, and Dipak Prajapati. "Indium-catalyzed microwave-accelerated pot economic C–C bond formation process towards the ‘dry-media’ synthesis of pyrimidine derivatives." RSC Advances 5, no. 17 (2015): 12506–10. http://dx.doi.org/10.1039/c4ra14434a.

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Substituted pyrimidines can be constructed in good yields via a microwave-accelerated C–C bond formation process through Lewis acid catalysed Diels–Alder reaction from easily available uracil diene and electron deficient acetylene carboxylate.

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9

Mach, Karel, Helena Antropiusová, Vladimír Hanuš, and Petr Sedmera. "Titanium-catalyzed Diels-Alder addition of bis(trimethylsilyl)acetylene to 1,3-cyclohexadiene." Collection of Czechoslovak Chemical Communications 54, no. 11 (1989): 3088–91. http://dx.doi.org/10.1135/cccc19893088.

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The TiCl4-(C2H5)2AlCl catalyst induced the Diels-Alder addition of bis(trimethylsilyl)acetylene to 1,3-cyclohexadiene affording 2,3-bis(trimethylsilyl)bicyclo[2.2.2]octa-2,5-diene in 72% yield under mild conditions. The product eliminates ethylene upon heating to 240 °C to give 1,2-bis(trimethylsilyl)benzene.

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10

Scott, L., and E. Fort. "Acetylene Equivalent for Bay Region Diels-Alder Cycloaddition." Synfacts 2010, no. 11 (2010): 1244. http://dx.doi.org/10.1055/s-0030-1258731.

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11

Bergmann, Ernst D. "Acetylene studies. V. Diels-alder reactions with methylchloroprene." Journal of Applied Chemistry 3, no. 4 (2007): 145–46. http://dx.doi.org/10.1002/jctb.5010030402.

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12

Anderson, MR, RFC Brown, KJ Coulston, FW Eastwood, and A. Ward. "The Pyrolysis of Phenylnaphthalenedicarboxylic Anhydrides: Products of Ring Contraction and of Radical Cyclization." Australian Journal of Chemistry 43, no. 7 (1990): 1137. http://dx.doi.org/10.1071/ch9901137.

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Naphthalene-1,2,-dicarboxylic anhydrides with neighbouring phenyl substituents give on flash vacuum pyrolysis (850-900°/0.02-0.04 mm) ring-contracted carbenes which insert into the phenyl groups. The 8- phenyl anhydride (7) gives acephenanthrylene (10) as the major product, and the 3-phenyl anhydride (15) gives 1,2 : 4,5-dibenzopentalene (indeno [2,1-a]indene) (18). The anhydrides (7) and (15) were � synthesized by pyrolysis of the corresponding 1-naphthylmethyl propynoates (2) and (13) through a new one-step process of intramolecular Diels -Alder addition/retro-Diels -Alder elimination of ace

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13

Hossaini, Zinatossadat, Faramarz Rostami-Charati, Fatemeh Sheikholeslami-Farahani, and Mahboubeh Ghasemian. "Synthesis of functionalized benzene using Diels–Alder reaction of activated acetylenes with synthesized phosphoryl-2-oxo-2H-pyran." Zeitschrift für Naturforschung B 70, no. 5 (2015): 355–60. http://dx.doi.org/10.1515/znb-2014-0261.

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AbstractAn effective one-pot synthesis of benzene derivatives using a Diels–Alder reaction of activated acetylenes with phosphoryl-2-oxo-2H-pyrans is described. The latter compounds were synthesized in good yield via the reaction of dialkyl acetylenedicarboxylates and alkyl bromides in the presence of trialkyl phosphites under solvent-free conditions at 50 oC.

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14

Cetin, Muge, Cansu Esen, Ozgun Daglar, et al. "1,3-Dipolar and Diels–Alder cycloaddition reactions on polyester backbones possessing internal electron-deficient alkyne moieties." Polymer Chemistry 7, no. 46 (2016): 7094–100. http://dx.doi.org/10.1039/c6py01827k.

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A polyester containing electron deficient internal alkyne units derived from acetylene dicarboxylic acid in the main backbone was employed as a polymeric platform in copper free cycloaddition reactions.

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15

Wagner, Bernd, Katrin Belger, Stefan Minkler, Volker Belting, and Norbert Krause. "Sustainable gold catalysis: synthesis of new spiroacetals." Pure and Applied Chemistry 88, no. 4 (2016): 391–99. http://dx.doi.org/10.1515/pac-2016-0406.

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AbstractVarious [O,O]- and [N,O]-spiroacetals were synthesized by gold-catalyzed spirocyclization of suitable functionalized alkynes. Whereas simple spiroacetals with two heteroatoms were readily obtained by regioselective cyclization of acetylenic diols or aminoalcohols, hitherto unknown spirocyclic isoxazolidines and pyrazolidines bearing three heteroatoms were formed by three-component coupling of alkynols, aldehydes, and protected hydroxylamine or hydrazine derivatives. The sustainability of these spirocyclizations was improved by using recyclable gold catalysts in water or nanomicelles as

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16

Ipaktschi, Junes. "Diels-Alder Reaction in the Presence of Zeolite." Zeitschrift für Naturforschung B 41, no. 4 (1986): 496–98. http://dx.doi.org/10.1515/znb-1986-0415.

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Cu(I) ion exchanged Y-zeolite catalyzed Diels-Alder reaction of furan, cyclopentadiene, 1.3-cyclohexadiene, isoprene and 2.3-dimethylbutadiene with a series of acrylic and acetylenic dienophiles is reported. The cycloadducts are obtained in high yield and selectivity

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17

Harrington, Laura E., James F. Britten та Michael J. McGlinchey. "Ferrocenyl-penta-(β-naphthyl)benzene Synthesis, structure, and dynamic behaviour". Canadian Journal of Chemistry 81, № 11 (2003): 1180–86. http://dx.doi.org/10.1139/v03-104.

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3-Ferrocenyl-2,4,5-tri-(β-naphthyl)cyclopentadienone undergoes a DielsAlder reaction with di-(β-naphthyl) acetylene to yield, after elimination of carbon monoxide, ferrocenyl-penta-(β-naphthyl)benzene (4). 1H and 13C variable-temperature NMR studies on 4 reveal the existence of multiple diastereoisomers at low temperature. These data are interpreted in terms of slowed rotation of the naphthyl groups, and are supported by the X-ray crystal structure of 4, which exhibits disorder at three of the naphthyl sites.Key words: sterically crowded molecules, hindered rotations, crystallography, NMR.

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18

McGlinchey, Michael J. "Diels-Alder Additions as Mechanistic Probes–Interception of Silyl-Isoindenes: Organometallic Derivatives of Polyphenylated Cycloheptatrienes and Related Seven-Membered Rings." Molecules 25, no. 20 (2020): 4730. http://dx.doi.org/10.3390/molecules25204730.

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The intermediacy of short-lived isoindenes, generated in the course of metallotropic or silatropic shifts over the indene skeleton, can be shown by Diels-Alder trapping with tetracyanoethylene, leading to the complete elucidation of the dynamic behaviour of a series of polyindenylsilanes. Cyclopentadienones, bearing ferrocenyl and multiple phenyl or naphthyl substituents undergo [4 + 2] cycloadditions with diaryl acetylenes or triphenylcyclopropene to form the corresponding polyarylbenzenes or cycloheptatrienes. The heptaphenyltropylium cation, [C7Ph7+], was shown to adopt a nonplanar shallow

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19

Erenler, Ramazan, Masaharu Uno, Thirumani Venkateshwar Goud, and Jean-François Biellmann. "Preparation of Some heterocyclic enones and ynones by isomerisation of the propargylic alcohols." Journal of Chemical Research 2009, no. 7 (2009): 459–64. http://dx.doi.org/10.3184/030823409x464467.

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The propargylic alcohols were synthesised by treatment of aldehydes with substituted acetylenes. The conversion of propargylic alcohols to propynones and propenones takes place with pyridine hydrochloride in methanol at room temperature. In presence of pyridinium triflate and p-toluenesulfonate the propynone was the only product isolated in the isomerisation of alcohol. The silylated propenone undergoes with cyclopentadiene a Diels–Alder cycloaddition to give ketone whose skeleton is related to that of quinine.

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20

Kumar, Perumal Raja. "A simple and versatile acetylene equivalent in Diels–Alder reactions." J. Chem. Soc., Chem. Commun., no. 8 (1989): 509–10. http://dx.doi.org/10.1039/c39890000509.

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21

Vijaya, R., T. C. Dinadayalane, and G. Narahari Sastry. "Diels–Alder reactions between cyclic five-membered dienes and acetylene." Journal of Molecular Structure: THEOCHEM 589-590 (August 2002): 291–99. http://dx.doi.org/10.1016/s0166-1280(02)00284-1.

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22

Saalfrank, Rolf W., Wieland Hafner, Joachim Markmann, Andreas Welch, Karl Peters, and Hans Georg von Schnering. "Einfache Synthese von 2,2-Diethoxy-2,5-dihydrofuranen, 2(5 H)Furanonen und 2-Ethoxy-furanen.Kristall-und Molekülstruktur eines Barrelenon Diels-Aider Produktes [1] / Convenient Synthesis of 2,2-Diethoxy-2,5-dihydrofurans, 2(5 H)Furanones and 2-Ethoxyfurans.Crystal and Molecular Structure of a Barrelenone Diels-Alder Product [1]." Zeitschrift für Naturforschung B 49, no. 3 (1994): 389–406. http://dx.doi.org/10.1515/znb-1994-0318.

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AbstractReaction of 1,2-hydroxyketones 5 with (2,2-diethoxyvinylidene)triphenylphosphorane (2) or (2,2-diethoxyvinyl)triphenylphosphonium tetrafluoroborates 6 yields the 2,2-diethoxy- 2.5-dihydrofurans 9. Depending on the reaction conditions used, the orthoesters 9 can be hydrolized to give 2(5 H)furanones 10 and 2-ethoxyfurans 11, respectively. 4,5-Dimethyl- 5.6-dihydro-2-pyranone (20) and 8-methoxycoumarin (23) are prepared, starting from (2,2-diethoxyvinyl)triphenylphosphonium tetrafluoroborate (6 a) and 1-hydroxy-2-methyl- 3-butanone (16) or 2-hydroxy-3-methoxy-benzaldehyde (21). The 2-eth

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23

Kuroda, Hirofumi, Ikuyoshi Tomita, and Takeshi Endo. "A Novel Polyaddition of Diols with Bifunctional Acetylenes Having Electron-Withdrawing Groups." Macromolecules 28, no. 2 (1995): 433–36. http://dx.doi.org/10.1021/ma00106a005.

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24

Larson, Gerald. "Some Aspects of the Chemistry of Alkynylsilanes." Synthesis 50, no. 13 (2018): 2433–62. http://dx.doi.org/10.1055/s-0036-1591979.

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In amongst the considerable chemistry of acetylenes there lies some unique chemistry of alkynylsilanes (silylacetylenes) some of which is reviewed herein. This unique character is exemplified not only in the silyl protection of the terminal C–H of acetylenes, but also in the ability of the silyl group to be converted into other functionalities after reaction of the alkynylsilane and to its ability to dictate and improve the regioselectivity of reactions at the triple bond. This, when combined with the possible subsequent transformations of the silyl group, makes their chemistry highly versatil

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25

Ogbomo, Sunny M., and D. Jean Burnell. "cis-3,5-Cyclohexadiene-1,2-diol derivatives: facial selectivity in their Diels–Alder reactions with ethylenic, acetylenic and azo dienophiles." Org. Biomol. Chem. 4, no. 20 (2006): 3838–48. http://dx.doi.org/10.1039/b607938e.

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26

Krishnan, R., and R. Sprycha. "Interactions of acetylenic diol surfactants with polymers." Colloids and Surfaces A: Physicochemical and Engineering Aspects 149, no. 1-3 (1999): 355–66. http://dx.doi.org/10.1016/s0927-7757(98)00605-0.

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27

Antol, Ivana, Luka Barešić, Zoran Glasovac, and Davor Margetić. "Computational Study of Electronic Influence of Guanidine Substitution on Diels-Alder Reactions of Heterocyclic Dienes." Croatica chemica acta 92, no. 2 (2019): 279–86. http://dx.doi.org/10.5562/cca3570.

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Quantum-chemical calculations of cycloaddition properties of cyclic heterodienes substituted with guanidine functionality were carried out. Molecular and electronic structures of series of dienes (pyrrole, furan, thiophene, isoindole and 1,3-butadiene) were calculated and reactivity order established on the basis of FMO theory. Transition state calculations of model [4+2] cycloaddition reaction with acetylene indicate that guanidine substitution influences reaction barriers in moderate extent (up to ~4 kcal mol–1). The substitution position plays an important role on the sign and magnitude of

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28

Lee, Albert W. M., W. H. Chan, and M. S. Wong. "Acetylenic sulphoxides in organic synthesis: Diels–Alder reactions." J. Chem. Soc., Chem. Commun., no. 24 (1988): 1585–86. http://dx.doi.org/10.1039/c39880001585.

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29

Lee, Albert W. M., W. H. Chan, Z. P. Zhong, K. F. Lee, and Anissa B. W. Yeung. "Synthesis and Diels–Alder Reaction of Acetylenic Sulfonate†." Journal of Chemical Research, no. 6 (1998): 326–27. http://dx.doi.org/10.1039/a800420j.

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30

Scott, Lawrence T. "Methods for the chemical synthesis of carbon nanotubes: an approach based on hemispherical polyarene templates." Pure and Applied Chemistry 89, no. 6 (2017): 809–20. http://dx.doi.org/10.1515/pac-2016-1222.

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AbstractHemispherical polyarenes represent attractive templates from which carbon nanotubes of the same diameter and rim structure (chirality) might be grown by repetitive annulation reactions. The resulting single-index (n,m) nanotubes would have one end open and the other end capped by the original template. Efforts in the author’s laboratory to synthesize (5,5) and (6,6) nanotube end-caps are described. Nitroethylene is shown to serve well as a “masked acetylene” for the conversion of polyarene bay regions into new unsubstituted benzene rings by a Diels-Alder cycloaddition/aromatization pro

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31

Khoshkholgh, Malihe Javan, Saeed Balalaie, Hamid R. Bijanzadeh, and Jürgen H. Gross. "Intramolecular domino-Knoevenagel-hetero-Diels-Alder reaction with terminal acetylenes." Arkivoc 2009, no. 9 (2008): 114–21. http://dx.doi.org/10.3998/ark.5550190.0010.908.

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32

Schneider, Thomas, Michael Keim, Bianca Seitz, and Gerhard Maas. "Reactions of 3-aryl-1-(trifluoromethyl)prop-2-yn-1-iminium salts with 1,3-dienes and styrenes." Beilstein Journal of Organic Chemistry 16 (August 24, 2020): 2064–72. http://dx.doi.org/10.3762/bjoc.16.173.

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3-Aryl-1-(trifluoromethyl)prop-2-yn-1-iminium triflate salts represent a novel, highly reactive class of acetylenic iminium salts. Herein we present several reactions which are based on the electron-poor acetylenic bond and on the high electrophilicity of the CF3-substituted iminium group. These salts were found to be highly reactive dienophiles in Diels–Alder reactions with cyclopentadiene, 2,3-dimethylbutadiene and even anthracene. At higher temperature, the cycloadducts undergo an intramolecular SE(Ar) reaction leading to condensed carbocycles incorporating a 1-(trifluoromethyl)-1-(dimethyl

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33

Shim, Seung-Bo, Yoon-Joo Ko, Byeong-Wook Yoo, Chang-Keun Lim та Jung-Hyu Shin. "Intramolecular Ionic Diels−Alder Reactions of α-Acetylenic Acetals". Journal of Organic Chemistry 69, № 23 (2004): 8154–56. http://dx.doi.org/10.1021/jo048867t.

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34

Froese, Robert D. J., James M. Coxon, Shawn C. West, and Keiji Morokuma. "Theoretical Studies of Diels−Alder Reactions of Acetylenic Compounds." Journal of Organic Chemistry 62, no. 20 (1997): 6991–96. http://dx.doi.org/10.1021/jo970811u.

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35

Diep, Nguyen T., та Luu D. Huy. "A Novel Scheme for the Synthesis of 21-Acetoxypregna-1,4,9(11)-triene- 17α,21-diol-3,20-dione from 9α-Hydroxyandrostenedione". Current Bioactive Compounds 16, № 5 (2020): 606–10. http://dx.doi.org/10.2174/1573407215666190308153507.

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Background: Vietnam currently imports up to 90% of the pharmaceuticals it consumes and 100% of the steroid-based pharmaceuticals. The ability for efficient chemical synthesis of the steroids could create commercial opportunities to address this issue. Synthesis of 21-acetoxypregna-1,4,9(11)- triene-17α,21-diol-3,20-dione is considered a key intermediate in the scheme of steroidal drug synthesis. Previous synthesis attempts of such steroids (corticoids) introduce a double bond at C-1(2) in the final stage of synthesis, which delivers a poor yield and reduces the economic efficiency of the proce

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36

Fort, Eric H., Matthew S. Jeffreys, and Lawrence T. Scott. "Diels–Alder cycloaddition of acetylene gas to a polycyclic aromatic hydrocarbon bay region." Chemical Communications 48, no. 65 (2012): 8102. http://dx.doi.org/10.1039/c2cc33885h.

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37

Williams, Richard Vaughan, Kamlesh Chauhan, and Vijay R. Gadgil. "1-Benzenesulfonyl-2-trimethylsilylacetylene: a new acetylene equivalent for the Diels–Alder reaction." J. Chem. Soc., Chem. Commun., no. 15 (1994): 1739–40. http://dx.doi.org/10.1039/c39940001739.

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38

Ma, Zhiyuan, Feng Ni, Grace H. C. Woo та ін. "An intramolecular inverse electron demand Diels–Alder approach to annulated α-carbolines". Beilstein Journal of Organic Chemistry 8 (6 червня 2012): 829–40. http://dx.doi.org/10.3762/bjoc.8.93.

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Intramolecular inverse electron demand cycloadditions of isatin-derived 1,2,4-triazines with acetylenic dienophiles tethered by amidations or transesterifications proceed in excellent yields to produce lactam- or lactone-fused α-carbolines. Beginning with various isatins and alkynyl dienophiles, a pilot-scale library of eighty-eight α-carbolines was prepared by using this robust methodology for biological evaluation.

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39

Rogers, Christine, and Brian A. Keay. "The effect of Lewis acids on the intramolecular Diels–Alder reaction of the furan diene." Canadian Journal of Chemistry 70, no. 12 (1992): 2929–47. http://dx.doi.org/10.1139/v92-375.

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A general method is described for effecting the intramolecular Diels–Alder reaction of the furan diene in which the side arm connecting the diene to the dienophile contains four carbon atoms. The use of 1.1 equivalents of methylaluminum dichloride at −78 °C for 2–8 h shifts the Diels–Alder equilibrium towards the products and provides the oxatricyclo adducts in good to excellent yield. Catalytic quantities of methylaluminum dichloride (10 mol%) provided a higher quantity of adduct than excess Lewis acid when the enone was substituted with alkyl groups. The scope was extended to include a precu

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40

Kranjc, Krištof, Amadej Juranovič, Marijan Kočevar, and Franc Perdih. "Supramolecular Diversity of Oxabicyclo[2.2.2]octenes Formed between Substituted 2H-Pyran-2-ones and Vinyl-Moiety-Containing Dienophiles." Symmetry 12, no. 10 (2020): 1714. http://dx.doi.org/10.3390/sym12101714.

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In Diels–Alder reactions, 2H-pyran-2-ones as dienes can yield a large variety of cycloadducts with up to four contiguous carbon stereogenic centers. Some of the potentially most useful, however difficult to prepare due to their low thermal stability, are the primary CO2-containing oxabicyclo[2.2.2]octenes, which could be formed as eight distinctive isomers (two sets of regioisomers, each of these composed of four different stereoisomers). A high-pressure synthesis of such products was recently described in a few cases where vinyl-moiety-containing dienophiles were used as synthetic equivalents

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41

Buttery, JH, J. Moursounidis, and D. Wege. "A,B-Diheteropentalenes by a Tandem Intramolecular Diels-Alder/Reverse Diels-Alder Reaction Sequence. Application to the Synthesis of Thieno[3,4-b]furan." Australian Journal of Chemistry 48, no. 3 (1995): 593. http://dx.doi.org/10.1071/ch9950593.

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Alkylation of 2-furylmethanethiol (28) with propargyl chloride gave the thioether (22) which on methoxycarbonylation afforded the acetylenic ester (30). On heating, this material underwent an intramolecular Diels -Alder reaction to give the tricyclic compound (32). In the presence of 3,6- di (pyridin-2′-yl)-s- tetrazine , (32) afforded methyl 4,6-dihydrothieno[3,4-b]furan-3-carboxylate (38) by a sequence involving a further Diels -Alder reaction followed by two reverse Diels-Alder reactions. The ester (38) could be dehydrogenated to give methyl thieno [3,4-b]furan-3-carboxylate (40) while hydr

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42

Mlostoń, Grzegorz, Paulina Grzelak, Maciej Mikina, Anthony Linden, and Heinz Heimgartner. "Hetero-Diels–Alder reactions of hetaryl and aryl thioketones with acetylenic dienophiles." Beilstein Journal of Organic Chemistry 11 (April 28, 2015): 576–82. http://dx.doi.org/10.3762/bjoc.11.63.

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Selected hetaryl and aryl thioketones react with acetylenecarboxylates under thermal conditions in the presence of LiClO4 or, alternatively, under high-pressure conditions (5 kbar) at room temperature yielding thiopyran derivatives. The hetero-Diels–Alder reaction occurs in a chemo- and regioselective manner. The initially formed [4 + 2] cycloadducts rearrange via a 1,3-hydrogen shift sequence to give the final products. The latter were smoothly oxidized by treatment with mCPBA to the corresponding sulfones.

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43

Mlostoń, Grzegorz, Paulina Grzelak, and Heinz Heimgartner. "Hetero-Diels–Alder reactions of hetaryl thiochalcones with acetylenic dienophiles." Journal of Sulfur Chemistry 38, no. 1 (2016): 1–10. http://dx.doi.org/10.1080/17415993.2016.1230857.

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44

Lee, Albert W. M., W. H. Chan, Z. P. Zhong, K. F. Lee, and Anissa B. W. Yeung. "ChemInform Abstract: Synthesis and Diels-Alder Reaction of Acetylenic Sulfonate." ChemInform 30, no. 14 (2010): no. http://dx.doi.org/10.1002/chin.199914037.

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CHAN, W. H., A. W. M. LEE, and K. M. LEE. "ChemInform Abstract: Acetylenic Sulfinates in Organic Synthesis: Diels-Alder Reactions." ChemInform 25, no. 35 (2010): no. http://dx.doi.org/10.1002/chin.199435063.

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46

Yoshizawa, Kazunari, Song-Yun Kang, Tokio Yamabe, Akinobu Naka, and Mitsuo Ishikawa. "Thermal Addition of Disilacyclobutenes and Acetylene: A Theoretical Study on Diels−Alder Type Reactions." Organometallics 18, no. 22 (1999): 4637–45. http://dx.doi.org/10.1021/om990316j.

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47

Coxon, James M., Stephen T. Grice, Robert G. A. R. Maclagan, and D. Quentin McDonald. "Ab initio Cs transition state for the Diels-Alder reaction of acetylene and butadiene." Journal of Organic Chemistry 55, no. 12 (1990): 3804–7. http://dx.doi.org/10.1021/jo00299a021.

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48

Greger, Harald. "Comparative Phytochemistry of Polyacetylenes of the Genus Artemisia (Asteraceae): Compounds with High Biological Activities and Chemotaxonomic Significance." Molecules 30, no. 3 (2025): 537. https://doi.org/10.3390/molecules30030537.

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In spite of the many chemical reports on polyacetylenes of the genus Artemisia, combined conclusions regarding their distribution and biological functions are widely missing. The aim of the present review was to arrange the diversity of polyacetylenes in the genus following biogenetic aspects and group them together into characteristic structural types. The co-occurrence of the dehydrofalcarinol type with the aromatic capillen-isocoumarin type represents a characteristic biogenetic trend, clearly segregating species of the subgenus Dracunculus from those of the subgenera Artemisia and Absinthi

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49

Andreica, Adriana Maria, Lucia Gansca, Irina Ciotlaus, and Ioan Oprean. "Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone." Revista de Chimie 68, no. 1 (2017): 180–85. http://dx.doi.org/10.37358/rc.17.1.5415.

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Were developed new and practical synthesis of (Z)-7-dodecene-1-yl acetate and (E)-9-dodecene-1-yl acetate. The routes involve, as the key step, the use of the mercury derivative of the terminal-alkyne w-functionalised as intermediate. The synthesis of (Z)-7-dodecene-1-yl acetate was based on a C6+C2=C8 and C8+C4=C12 coupling scheme, starting from 1,6-hexane-diol. The first coupling reaction took place between 1-tert-butoxy-6-bromo-hexane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-oct-7-yne, which is transformed in di[tert-butoxy-oct-7-yne]mercury. The mercury derivati

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50

Singleton, Daniel A., and Jose P. Martinez. "2-Trimethylsilylvinylboranes: highly reactive and selective diels-alder equivalents of 2-trimethylsilylvinyl alcohol and acetylene." Tetrahedron Letters 32, no. 50 (1991): 7365–68. http://dx.doi.org/10.1016/0040-4039(91)80108-i.

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