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Relevant bibliographies by topics / Cyclopropane ring formation

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Academic literature on the topic 'Cyclopropane ring formation'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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Journal articles on the topic "Cyclopropane ring formation"

1

Kohout, Ladislav. "The synthesis of 5,6-cyclopropanocholestanes with oxygen functions in positions 3 and 7." Collection of Czechoslovak Chemical Communications 51, no. 2 (1986): 429–35. http://dx.doi.org/10.1135/cccc19860429.

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The Simmons-Smith methylenation of the double bond in 3β-acetoxycholest-5-en-7-ols takes place selectively under formation of an adduct the configuration of which is determined by the configuration of the 7-hydroxyl group: 7β-alcohol IV gave 5β,6β-cyclopropane derivative VI, 7α-alcohol V gave 5α,6α-cyclopropane derivative VIII. On photochemically initiated cyclization of 3β-acetoxy-B-homo-5-en-7a-one (XIII) we obtained the product with an α-cyclopropane ring exclusively, i.e. 3β-acetoxy-5,6α-cyclopropano-5α-cholestan-7-one (XII).

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2

Vereshchagin, Anatolii N., Michail N. Elinson, Nikita O. Stepanov, and Gennady I. Nikishin. "New Way to Substitute Tetracyanocyclopropanes: One-Pot Cascade Assembling of Carbonyls and Malononitrile by the Only Bromine Direct Action." ISRN Organic Chemistry 2011 (July 26, 2011): 1–5. http://dx.doi.org/10.5402/2011/469453.

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The new type of the chemical cascade reaction was found: formation of cyclopropanes from carbonyl compounds and CH acid by the only bromine direct action. The action of aqueous bromine on the carbonyl compounds and malononitrile in EtOH-H2O solutions in the presence of NaOAc results in the formation of 3-substituted 1,1,2,2-tetracyanocyclopropanes in 48–93% yields. The latter are well-known precursors for the different bicyclic heterosystems, among them those containing cyclopropane ring and those possessing different types of pharmacological activity.

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3

Edwards, Oliver E., Dusan Dvornik, Ralph J. Kolt, and Barbara A. Blackwell. "Formation, reactions, and NMR spectra of 1,20-cycloatidanes." Canadian Journal of Chemistry 70, no. 5 (1992): 1397–405. http://dx.doi.org/10.1139/v92-178.

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Imines derived from the alkaloid atisine gave N-acetyl 1,20-cycloatidane derivatives when heated with acetic anhydride. Vigorous alkaline hydrolysis cleaved the cyclopropane ring, regenerating the parent imine. The 1H and 13C NMR spectra of several 1,20-cyclo derivatives have been assigned and compared to those of the parent imines 2. All of the N-acetyl compounds showed doubling of the majority of the NMR resonances, due to amide rotamers. The effects of the cyclopropane ring current are noted.

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4

Grogan, D. W., and J. E. Cronan. "Cyclopropane ring formation in membrane lipids of bacteria." Microbiology and Molecular Biology Reviews 61, no. 4 (1997): 429–41. http://dx.doi.org/10.1128/mmbr.61.4.429-441.1997.

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It has been known for several decades that cyclopropane fatty acids (CFAs) occur in the phospholipids of many species of bacteria. CFAs are formed by the addition of a methylene group, derived from the methyl group of S-adenosylmethionine, across the carbon-carbon double bond of unsaturated fatty acids (UFAs). The C1 transfer does not involve free fatty acids or intermediates of phospholipid biosynthesis but, rather, mature phospholipid molecules already incorporated into membrane bilayers. Furthermore, CFAs are typically produced at the onset of the stationary phase in bacterial cultures. CFA

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Grogan, D. W., and J. E. Cronan. "Cyclopropane ring formation in membrane lipids of bacteria." Microbiology and molecular biology reviews : MMBR 61, no. 4 (1997): 429–41. http://dx.doi.org/10.1128/.61.4.429-441.1997.

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6

Zhang, Wei, and Paul Dowd. "Unusual cyclopropane formation following free radical ring expansion." Tetrahedron Letters 33, no. 48 (1992): 7307–10. http://dx.doi.org/10.1016/s0040-4039(00)60173-9.

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7

Allen, F. H., J. P. M. Lommerse, V. J. Hoy, J. A. K. Howard та G. R. Desiraju. "The hydrogen-bond C–H donor and π-acceptor characteristics of three-membered rings". Acta Crystallographica Section B Structural Science 52, № 4 (1996): 734–45. http://dx.doi.org/10.1107/s0108768196005319.

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Crystallographic results, retrieved from the Cambridge Structural Database, show that the C--H protons of cyclopropane, aziridine and oxirane form C—H...O (particularly C—H...O—C) hydrogen bonds. The frequency of formation and geometrical characteristics of these bonds indicate a bond-strength ordering: Csp 1—H...O > C(ring)—H...O ≃ Csp 2—H...O > Csp 3—H...O, which is in excellent agreement with the well known ethylenic properties of C(ring)—H and with residual δ+ charges calculated for these systems. There is some evidence to suggest that C=C—H in cyclopropene, known to be a highly acid

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8

Bisag, Giorgiana Denisa, Pietro Viola, Luca Bernardi, and Mariafrancesca Fochi. "Divergent Reactivity of D-A Cyclopropanes under PTC Conditions, Ring-Opening vs. Decyanation Reaction." Catalysts 13, no. 4 (2023): 760. http://dx.doi.org/10.3390/catal13040760.

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The divergent reactivity of D-A cyclopropane, under PTC conditions, is herein reported. Thus, a ring-opening or a decyanation reaction can be achieved by reacting 2-arylcyclopropane-1,1-dicarbonitriles 1 with thioacetic acid in different reaction conditions. The use of solid Cs2CO3 leads unexpectedly to the synthesis of new D-A cyclopropane derivatives via a decyanation reaction, followed by diastereoselective acetylation, whereas the use of an aqueous solution of Cs2CO3 results in a typical ring-opening reaction with the formation of S-thiolate products. Therefore, the use of tailored reactio

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9

Pyne, Stephen G., Karl Schafer, Brian W. Skelton, and Allan H. White. "Asymmetric Synthesis of Protected 2-Substituted Cyclopropane Amino Acids." Australian Journal of Chemistry 51, no. 2 (1998): 127. http://dx.doi.org/10.1071/c97105.

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The cyclopropanation reactions of (1a) with ethyl and t-butyl (dimethylsulfuranylidene)acetate proceeded with good diastereoselectivity and resulted in the formation of three diastereoisomeric products. The major diastereoisomeric product ((2a) and (2b), respectively) could be isolated in pure form by simple recrystallization. The stereochemistry of the major cyclopropane product (2b) has been determined by single-crystal X-ray structural analysis. These cyclopropanation products were susceptible to ring opening of the cyclopropane ring upon reduction with sodium borohydride or acid hydrolysis

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Marson, Charles M., Catriona A. Oare, Jane McGregor, Timothy Walsgrove, Trevor J. Grinter, and Harry Adams. "A sequential stereocontrolled cyclopropane ring formation and semi-pinacol rearrangement." Tetrahedron Letters 44, no. 1 (2003): 141–43. http://dx.doi.org/10.1016/s0040-4039(02)02511-x.

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Dissertations / Theses on the topic "Cyclopropane ring formation"

1

Podder, Ranjan Kumar. "Formation and cleavage of cyclopropane ring systems and related studies." Thesis, University of North Bengal, 1986. http://hdl.handle.net/123456789/848.

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2

Johnson, William T. G. "Synthesis of precursors of a highly pyramidalized alkene and ab initio calculations on methylenecyclopropane, cyclopropene, and 1,3-diradicals /." Thesis, Connect to this title online; UW restricted, 1999. http://hdl.handle.net/1773/11586.

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3

Hewitt, Russell James. "Investigations of ring-opening reactions of cyclopropanated carbohydrates : towards the synthesis of the natural product (--)-TAN-2483B : a thesis submitted to the Victoria University of Wellington in fulfilment of the requirements for the degree of Doctor of Philosophy in Chemistry /." ResearchArchive@Victoria e-Thesis, 2010. http://hdl.handle.net/10063/1249.

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Lehmann, Anna Louise. "gem-Dihalocyclopropanes as precursors to alkaloidal ring systems." Phd thesis, 2010. http://hdl.handle.net/1885/150781.

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gem-Dihalocyclopropanes (1) are an important class of compound that play significant roles in contemporary organic synthesis. This is largely due to their ease of preparation, (which is normally accomplished via addition of the relevant dihalocarbene to an alkene), and the wide range of reactions they can undergo. These reactions can be divided into two broad subgroups, those that proceed with retention of the three membered ring, and those where one of the C-C bonds is broken, thus leading to ring cleavage. The vast majority of gem-dihalocyclopropanes described in the literature are the dibro

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Sydnes, Magne Olav. "Applications of gem-Dihalocyclopropanes in synthesis." Phd thesis, 2004. http://hdl.handle.net/1885/150075.

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Phillis, Andrew Toroa. "Applications of gem-dichlorocyclopropanes in chemical synthesis." Phd thesis, 2008. http://hdl.handle.net/1885/150970.

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Book chapters on the topic "Cyclopropane ring formation"

1

Merino, P. "Direct Formation of the Cyclopropane Ring." In Monocyclic Arenes, Quasiarenes, and Annulenes. Georg Thieme Verlag KG, 2010. http://dx.doi.org/10.1055/sos-sd-045-00192.

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2

Roy, M. N., V. N. G. Lindsay, and A. B. Charette. "Cyclopropane Formation by Ring-Closure Reactions." In Stereoselective Synthesis 1 Stereoselective Reactions of Carbon—Carbon Double Bonds. Georg Thieme Verlag KG, 2011. http://dx.doi.org/10.1055/sos-sd-201-00417.

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3

Roy, M. N., V. N. G. Lindsay, and A. B. Charette. "Cyclopropane Formation by Ring-Contraction Reactions." In Stereoselective Synthesis 1 Stereoselective Reactions of Carbon—Carbon Double Bonds. Georg Thieme Verlag KG, 2011. http://dx.doi.org/10.1055/sos-sd-201-00420.

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4

Abu Ali, H., V. M. Dembitsky, and M. Srebnik. "Cyclopropane Ring Formation via Hydroboration of Allylic Halides." In Boron Compounds. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-006-00902.

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5

Lambert, Tristan H. "C–O Ring Formation." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0049.

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A reductive radical cyclization of tetrahydropyran 1 to form bicycle 2 using iron(II) chloride in the presence of NaBH4 was reported (Angew. Chem. Int. Ed. 2012, 51, 6942) by Louis Fensterbank and Cyril Ollivier at the University of Paris and Anny Jutand at the Ecole Normale Supérieure. The enantioselective conversion of tetrahydrofuran 3 to spirocycle 5 via iminium ion-catalyzed hydride transfer/cyclization was developed (Angew. Chem. Int. Ed. 2012, 51, 8811) by Yong-Qiang Tu at Lanzhou University. Daniel Romo at Texas A&M University showed (J. Am. Chem. Soc. 2012, 134, 13348) that enanti

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Lambert, Tristan H. "C–O Ring Formation." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0044.

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The enantioselective bromocyclization of dicarbonyl 1 to form dihydrofuran 3 using thiocarbamate catalyst 2 was developed (Angew. Chem. Int. Ed. 2013, 52, 8597) by Ying-Yeung Yeung at the National University of Singapore. Access to dihydrofuran 5 from the cyclic boronic acid 4 and salicylaldehyde via a morpholine-mediated Petasis borono-Mannich reaction was reported (Org. Lett. 2013, 15, 5944) by Xian-Jin Yang at East China University of Science and Technology and Jun Yang at the Shanghai Institute of Organic Chemistry. Chiral phosphoric acid 7 was shown (Angew. Chem. Int. Ed. 2013, 52, 13593)

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7

Taber, Douglass F. "The Vanderwal Synthesis of Echinopine B." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0099.

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Intramolecular cyclopropanation has long been a powerful strategy for stereoselective polycarbocyclic construction. For many years, this was limited to diazo carbonyl insertion. More recently, alternative strategies for intramolecular cyclopropane construction have been developed. The power of such an approach is illustrated by the total synthesis of echinopine B 3 reported (Angew. Chem. Int. Ed. 2012, 51, 7572) by Christopher D. Vanderwal of the University of California, Irvine. The starting material for the synthesis was the commercial keto ester 4. Enol ether formation followed by cycloprop

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8

Lambert, Tristan H. "Reactions Involving Carbon–Carbon Bond Cleavage." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0028.

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Although they have historically played a relatively lesser role in organic synthesis, the appearance of a number of interesting methods that utilize C–C bond cleavage has prompted coverage in this chapter. Christopher W. Bielawski at the University of Texas at Austin found (Chem. Sci. 2012, 3, 2986) that the diamidocarbene 1 inserted into the C(O)–C(O) bond of dione 2 to produce 3 at room temperature. The use of oxalate monoester 5 for the decarboxylative cross-coupling with pyridine 4 to produce 6 was reported (Tetrahedron Lett. 2012, 53, 5796) by Yi-Si Feng at Hefei University of Technology.

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Taber, Douglass. "Stereocontrolled Carbocyclic Construction: The Mulzer Synthesis of (-)-Penifulvin A." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0082.

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Tanmaya Pathak of the Indian Institute of Technology, Kharagpur devised (J. Org. Chem. 2009, 74, 2710) a preparation of enantiomerically-pure oxygenated cyclopropanes such as 3 from carbohydrate precursors. Andrei K. Yudin of the University of Toronto established (Organic Lett. 2009, 11, 1281) a route to aminated cyclobutanes such as 5 based on sigmatropic rearrangement of the β-lactam 4. Tanmaya Pathak of the Indian Institute of Technology, Kharagpur devised ( J. Org. Chem. 2009 , 74 , 2710) a preparation of enantiomerically-pure oxygenated cyclopropanes such as 3 from carbohydrate precursors

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Taber, Douglass F. "Alkene and Alkyne Metathesis: (+)-Anamarine (Sabitha), ( ± )-Pseudotabersonine (Martin), Lactimidomycin (Fürstner)." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0034.

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Masato Matsugi of Meijo University showed (J. Org. Chem. 2010, 75, 7905) that over five iterations, the fluorous-tagged Ru catalyst 1b was readily recovered and reused for the cyclization of 2 to 3. Hengquan Yang of Shanxi University reported (Chem. Commun. 2010, 46, 8659) that the Hoveyda catalyst 1a encapsulated in mesoporous SBA-1 could also be reused several times. Jean-Marie Basset of KAUST Catalysis Center, Régis M. Gauvin of Université Lille, and Mostafa Taoufik of Université Lyon 1 described (Chem. Commun. 2010, 46, 8944) a W catalyst on silica that was also active for alkene metathesi

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