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Journal articles on the topic 'Sigmatropic rearrangements'

Author: Grafiati

Published: 4 June 2021

Last updated: 11 June 2025

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1

Zhang, Lei, Mengjie Hu, and Bo Peng. "[3,3]- and [5,5]-Sigmatropic Rearrangements of Aryl Sulfoxides Using An ‘Assembly/Deprotonation’ Technology." Synlett 30, no. 20 (2019): 2203–8. http://dx.doi.org/10.1055/s-0039-1690212.

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The redox-neutral ortho-functionalizations of aryl/heteroaryl sulfoxides via interrupted Pummerer processes have been greatly advanced since its discovery by Kita and Padwa in the early 2000s. In this context, we recently developed an ortho-cyanoalkylation of aryl sulfoxides with alkyl nitriles using an ‘assembly/deprotonation’ protocol. The success of the reaction hinges on the independent control of the electrophilic assembly of both coupling partners and subsequent deprotonation of the in situ generated imine sulfonium intermediates. Further [3,3]-sigmatropic rearrangement of the in situ formed ketenimine sulfonium species furnishes ortho-cyanoalkylated aryl sulfides. More recently, we also applied the ‘assembly/deprotonation’ strategy for the development of the [5,5]-sigmatropic rearrangement of aryl sulfoxides with allyl nitriles that allows for para-cyanoalkylation of aryl sulfoxides. The development of these two reactions is described in this Synpacts article.1 Background2 [3,3]-Sigmatropic Rearrangement3 [5,5]-Sigmatropic Rearrangement4 Conclusion

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2

Zhang, Beibei, Xiaoxian Li, Boying Guo, and Yunfei Du. "Hypervalent iodine reagent-mediated reactions involving rearrangement processes." Chemical Communications 56, no. 91 (2020): 14119–36. http://dx.doi.org/10.1039/d0cc05354f.

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We summarize the developments of hypervalent iodine reagents-mediated reactions involving [1,2]-migration, Hofmann rearrangement, Beckmann rearrangement, ring contraction/expansion, [3,3]-sigmatropic/iodonium-Claisen rearrangement and some miscellaneous rearrangements.

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3

Nohira, Hiroyuki, and Toshiyuki Nohira. "Dynamic correlation diagrams for sigmatropic reactions based on orbital phase conservation theory." Journal of Theoretical and Computational Chemistry 16, no. 06 (2017): 1750055. http://dx.doi.org/10.1142/s0219633617500559.

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For sigmatropic reactions, such as [1,3] and [1,5] hydrogen shifts, the Cope and Claisen rearrangements, and the Berson–Nelson rearrangement, no correlation diagrams consistent with the classical electronic formulas have been reported. Here, we report dynamic correlation diagrams for these sigmatropic reactions based on orbital phase conservation theory. The diagrams are consistent with both the selection rules of sigmatropic reactions proposed by Woodward and Hoffmann and classical electronic formulas.

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4

Ficeri, Vlastimír, Peter Kutschy, Milan Dzurilla, and Ján Imrich. "[3,3]- Versus [1,3]-Sigmatropic Rearrangement of O-Substituted Allyl N-Acylmonothiocarbamates." Collection of Czechoslovak Chemical Communications 59, no. 12 (1994): 2650–62. http://dx.doi.org/10.1135/cccc19942650.

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Substituted allylic alcohols (2-buten-1-ol, 1-buten-3-ol, cinnamyl alcohol and 3-methyl-2-buten-1-ol) react with acyl isothiocyanates (4-chlorobenzoyl, 2,6-difluorobenzoyl, 3-phenylpropenoyl, 2-thienocarbonyl, 3-chloro-2-thienocarbonyl and 3-chloro-2-benzo[b]thienocarbonyl isothiocyanate) with the formation of highly reactive O-substituted allyl N-acylmonothiocarbamates, which either spontaneously or by heating in boiling benzene undergo [3,3]-sigmatropic rearrangement to S-substituted allyl N-acylmonothiocarbamates. The structure of S-esters with isomerized allylic group affords the unequivocal evidence of the [3,3]-sigmatropic route of studied rearrangement. Further heating of [3,3]-rearranged N-(4-chlorobenzoyl)monothiocarbamates results in the [1,3]-sigmatropic shift of monothiocarbamate group. Using arylalkyl alcohols with the allylic double bond inserted into an aromatic system the obtained O-esters either do not undergo any rearrangement (benzyl alcohol) or undergo [1,3]-sigmatropic rearrangement (2- and 3-furylmethanol and 1-(2-furyl)ethanol) to the corresponding S-esters. For explanation of this reaction the tandem of [3,3]- and [1,3]-sigmatropic rearrangements is suggested.

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5

Dudziński, Piotr, Wibke S. Husstedt, Andrej V. Matsnev, Joseph S. Thrasher, and Günter Haufe. "Synthesis and [3,3]-sigmatropic rearrangements of 5-(pentafluorosulfanyl)-pent-3-en-2-ol, its homologues, and trifluoromethyl analogues." Organic & Biomolecular Chemistry 19, no. 25 (2021): 5607–23. http://dx.doi.org/10.1039/d1ob00870f.

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[3,3]-Sigmatropic rearrangements based on different SF<sub>5</sub>-substituted allylic alcohols were investigated. The synthetic sequence developed for SF<sub>5</sub> compounds is also useful for CF<sub>3</sub> analogues and its application in Johnson–Claisen rearrangement.

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6

Zeh, J., and M. Hiersemann. "ChemInform Abstract: Sigmatropic Rearrangements." ChemInform 42, no. 42 (2011): no. http://dx.doi.org/10.1002/chin.201142241.

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7

Villalva-Servín, Nidia P., Alain Laurent, and Alex G. Fallis. "Part 2: Efficient strategies for the construction of variably substituted bicyclo[5.3.1]undecenones (AB-taxane ring systems) and their conversion to tricyclo[9.3.1.03,8]pentadecenones (ABC taxane ring systems) and bicyclo[2.2.2]octanones." Canadian Journal of Chemistry 82, no. 2 (2004): 227–39. http://dx.doi.org/10.1139/v03-201.

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The extension of our strategies for the construction of cyclic molecules containing variably substituted bicyclo[5.3.1]undecenones (AB taxane ring systems) for the synthesis of the tricyclo[9.3.1.03,8]pentadecenone (ABC taxane ring system) and bicyclo[2.2.2]octanones are described. These routes employ a multi-component coupling protocol that employs sequential magnesium-mediated carbometallation of allyl-substituted propargyl alcohols followed by diastereoselective Lewis acid catalyzed intramolecular DielsAlder reactions (IMDA). Subsequent ring-closing metathesis (RCM) afforded the ABC taxane core structure. Enone accelerated [3,3] sigmatropic rearrangements (Cope rearrangements) generated the bicyclo[2.2.2]octanone nucleus. In the presence of a Lewis acid, the dienophile precursor underwent a tandem reaction via the adduct directly to the bicyclo[2.2.2]octanones. This is the first example of a novel enone accelerated carbocycle Cope rearrangement and provides direct access to bicyclo[2.2.2]octanones by a new route that compliments the traditional cyclohexadiene cycloaddition approach. Key words: magnesium chelate, Lewis acid, taxanes, DielsAlder, sigmatropic rearrangement, oxy-Cope, ring-closing metathesis, bicyclo[2.2.2]octanone.

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8

Belaissaoui, Abdelhak, Sandrine Jacquot, Claude Morpain, Gérard Schmitt, Joël Vebrel, and Bernard Laude. "Réactivité dipolaire-1,3 du 4,4,4-trichiloro-3-éthoxycarbonylamino-2-diazobutyrate d'éthyle issu de l'action du diazoacétate d'éthyle sur la N-éthoxycarbonyl-N-(2,2,2-trichloroéthylidène)amine." Canadian Journal of Chemistry 75, no. 5 (1997): 523–30. http://dx.doi.org/10.1139/v97-061.

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The reaction of ethyl diazoacetate with the N-ethoxycarbonyl-N-(2,2,2-trichloroethylidene)amine yields, by a nucleophilic addition, a new diazo compound that gives 1,3-dipolar cycloaddition reactions with acetylenic esters and maleimides. With acetylenic esters, the cycloadduct leads to substituted pyrazoles by [1,5] sigmatropic rearrangements. With maleimides, we observe a diastereospecific cycloaddition reaction. The intermediary cycloadduct evolves by nitrogen elimination to give a maleimidocyclopropane. The diastereospecificity was explained by an endo-anti approach of the reactants. Keywords: N-ethoxycarbonyl-N-(2,2,2-trichloroethylidene)amine, ethyl diazoacetate, nucleophilic addition, 1,3-dipolar cycloaddition, sigmatropic rearrangement, diastereoselectivity.

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9

Ernouf, Guillaume, Jean-Louis Brayer, Christophe Meyer, and Janine Cossy. "Sigmatropic rearrangements of cyclopropenylcarbinol derivatives. Access to diversely substituted alkylidenecyclopropanes." Beilstein Journal of Organic Chemistry 15 (February 5, 2019): 333–50. http://dx.doi.org/10.3762/bjoc.15.29.

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Cyclopropenes constitute useful precursors of other classes of compounds incorporating a three-membered ring. Although the transformation of substituted cyclopropenes into alkylidenecyclopropanes can be accomplished through different strategies, this review is focusing specifically on the use of [2,3]- and [3,3]-sigmatropic rearrangements involving cyclopropenylcarbinol derivatives as substrates. These sigmatropic rearrangements, which have been developed in recent years, allow a remarkably efficient and stereoselective access to a wide variety of heterosubstituted and/or functionalized alkylidenecyclopropanes which would not be readily accessible by other strategies. The different [2,3]- and [3,3]-sigmatropic rearrangements of cyclopropenylcarbinol derivatives disclosed to date, as well as the analysis of their substrate scope and some applications of the products arising from those reactions, are presented in this review.

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10

Frampton, Christopher S., Michael W. Majchrzak, and John Warkentin. "Sense of sequential 1,5-sigmatropic rearrangements of dimethyl-3,3-dialkyl-3H-pyrazole-4,5-dicarboxylates. Crystal and molecular structures of two dimethyl-4,5-dialkyl-1H-pyrazole-1,3-dicarboxylates." Canadian Journal of Chemistry 69, no. 3 (1991): 373–78. http://dx.doi.org/10.1139/v91-057.

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3,3-Dialkyl-3H-pyrazole-4,5-dicarboxylic acid dimethyl esters (4), obtained by cycloaddition of R1R2C=N+=N− (R1 = R2 = CH3; R1 = CH3, R2 = CH2CH3) to CH3O2CC≡CCO2CH3, rearrange thermally by 1,5-sigmatropic alkyl shifts to both N and C. The latter rearrangement is followed by two successive 1,5-sigmatropic shifts of a methoxycarbonyl group. Final products of the threefold rearrangement were shown to be 4,5-dialkyl-1H-pyrazole-1,3-dicarboxylic acid dimethyl esters (6), rather than the isomeric 3,4-dialkyl-1H-pyrazole-1,5-dicarboxylic acid dimethyl esters (7), by means of single crystal X-ray diffraction. Those products therefore result from alkyl migration to C-4 of 4, followed by sequential migration of the methoxycarbonyl group, initially at C-4, to C-3 and then to N-2 of 4. In the initial alkyl migration step, ethyl migrates in preference to methyl, and in subsequent migration steps the methoxycarbonyl group migrates faster than the ethyl or methyl group. Crystals of 4-ethyl-5-methyl-1H-pyrazole-1,3-dicarboxylic acid dimethyl ester (6b) are monoclinic, of space group P21/n, with a = 7.907(1) Å, b = 11.087(2) Å, c = 13.199(3) Å, V = 1124.9(4) Å 3, Dc = 1.34 g cm−3, Dm = 1.33 g cm−3 for Z = 4, and R1 = 0.0772 (R2 = 0.0626) for 1474 reflections (R1 = 0.0428, R2 = 0.0422 for 903 reflections with I > 3σ(I)). The structure of 6a is similar. Key words: 3,3-dialkyl-3H-pyrazoles, 1,5-sigmatropic rearrangements of; 4,5-dialkyl-1H-pyrazoles, crystal and molecular structures; 1,5-sigmatropic rearrangements of pyrazoles, sense of.

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11

Andreev, V. G., A. F. Kolomiets, and A. V. Fokin. "[3,3]-Sigmatropic rearrangements of fluorocarbanions." Journal of Fluorine Chemistry 56, no. 3 (1992): 259–69. http://dx.doi.org/10.1016/s0022-1139(00)81173-2.

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12

Frija, Luís M. T., Igor Reva, Amin Ismael, Daniela V. Coelho, Rui Fausto, and M. Lurdes S. Cristiano. "Sigmatropic rearrangements in 5-allyloxytetrazoles." Organic & Biomolecular Chemistry 9, no. 17 (2011): 6040. http://dx.doi.org/10.1039/c1ob05460k.

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13

Sweeney, J. B. "Sigmatropic rearrangements of ‘onium’ ylids." Chemical Society Reviews 38, no. 4 (2009): 1027. http://dx.doi.org/10.1039/b604828p.

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14

Kobbelgaard, Sara, Sebastian Brandes, and Karl Anker Jørgensen. "Asymmetric Organocatalysed [1,3]-Sigmatropic Rearrangements." Chemistry - A European Journal 14, no. 5 (2008): 1464–71. http://dx.doi.org/10.1002/chem.200701729.

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15

Hwu, Jih Ru, and Denise A. Anderson. "Zwitterion-accelerated [3,3]-sigmatropic rearrangements and [2,3]sigmatropic rearrangements of sulphoxides and amine oxides." Journal of the Chemical Society, Perkin Transactions 1, no. 12 (1991): 3199. http://dx.doi.org/10.1039/p19910003199.

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16

Reissig, Hans-Ulrich, Gesine Böttcher, and Reinhold Zimmer. "New 1,3-dihydroazepin-2-one derivatives by [3,3]-sigmatropic rearrangement of suitably substituted 2-alkenylcyclopropyl isocyanates." Canadian Journal of Chemistry 82, no. 2 (2004): 166–76. http://dx.doi.org/10.1139/v03-186.

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The 2-siloxysubstituted 2-alkenylcyclopropanecarboxylic acids 1014 were converted into the corresponding carbonyl azides by treatment with DPPA (diphenyl phosphorazidate) and triethylamine. On heating to 80 °C these intermediates smoothly furnished azepinone derivatives 1925 in moderate to good overall yields, which are the result of a sequence of Curtius reaction to cyclopropylisocyanates, [3,3]-sigmatropic rearrangement, and a final proton shift. The primary products may undergo desilylation (to afford azepin-2,5-diones such as 23) or double bond migration (to compound 25). Cyclopropanecarboxylic acids cis-32, cis-34, and cis-35, which bear no 2-siloxy group, similarly provided azepinone derivatives 3638 in good yields. No influence of the 2-siloxy substituent on the reaction course and rates could be observed in these qualitative studies, which was confirmed by DFT calculations with model compounds 3942 showing similar reaction barriers for rearrangements of cyclopropylisocyanates with or without a 2-hydroxy group.Key words: vinyl cyclopropanes, carbonylazides, [3.3]-sigmatropic rearrangements, azepinones.

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17

Boyle, Peter H., Haslin Dato Paduka Ali, and Thomas J. Mc Donald. "Sigmatropic rearrangements of 2,4-dinitrophenyl oximes." Arkivoc 2003, no. 7 (2003): 67–79. http://dx.doi.org/10.3998/ark.5550190.0004.708.

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18

Purrington, Suzanne T., and Sonia C. Weeks. "[3,3]-Sigmatropic rearrangements of fluorinated compounds." Journal of Fluorine Chemistry 56, no. 2 (1992): 165–73. http://dx.doi.org/10.1016/s0022-1139(00)81099-4.

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19

Sweeney, J. B., Ali Tavassoli, Neil B. Carter, and Jerome F. Hayes. "[2,3]-Sigmatropic rearrangements of didehydropiperidinium ylids." Tetrahedron 58, no. 51 (2002): 10113–26. http://dx.doi.org/10.1016/s0040-4020(02)01397-2.

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20

WILSON, S. R. "ChemInform Abstract: Anion-Assisted Sigmatropic Rearrangements." ChemInform 25, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.199403271.

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21

Maulide, Nuno, Xueliang Huang, and Sebastian Klimczyk. "Charge-Accelerated Sulfonium [3,3]-Sigmatropic Rearrangements." Synthesis 2012, no. 02 (2011): 175–83. http://dx.doi.org/10.1055/s-0031-1289632.

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22

Minkin, Vladimir I., Igor E. Mikhailov, and Galina A. Dushenko. "Novel degenerate sigmatropic rearrangements of amidines." Journal of the Chemical Society, Chemical Communications, no. 17 (1988): 1181. http://dx.doi.org/10.1039/c39880001181.

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23

Yu, Yue, Wei Huang, Yang Chen, Bingjie Gao, Wanqing Wu, and Huanfeng Jiang. "Calcium carbide as the acetylide source: transition-metal-free synthesis of substituted pyrazoles via [1,5]-sigmatropic rearrangements." Green Chemistry 18, no. 24 (2016): 6445–49. http://dx.doi.org/10.1039/c6gc02776h.

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24

HWU, J. R., and D. A. ANDERSON. "ChemInform Abstract: Zwitterion-Accelerated (3,3)-Sigmatropic Rearrangements and (2,3)- Sigmatropic Rearrangements of Sulfoxides and Amine Oxides." ChemInform 23, no. 13 (2010): no. http://dx.doi.org/10.1002/chin.199213099.

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25

Mingat, Gaëlle, Joseph J. W. McDouall, and Jonathan Clayden. "Dihydrothiophenes containing quaternary stereogenic centres by sequential stereospecific rearrangements and ring-closing metathesis." Chem. Commun. 50, no. 51 (2014): 6754–57. http://dx.doi.org/10.1039/c4cc02596b.

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26

Deslongchamps, Ghislain, and Pierre Deslongchamps. "Bent bonds and the antiperiplanar hypothesis – a simple model to rationalize [1,3]-sigmatropic alkyl shifts." Organic & Biomolecular Chemistry 14, no. 32 (2016): 7754–67. http://dx.doi.org/10.1039/c6ob01139j.

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27

López, Roberto Villar, Olalla Nieto Faza, and Carlos Silva López. "Conformational control allows for [3,3]-sigmatropic rearrangements to proceed with torquoselectivity." RSC Advances 6, no. 64 (2016): 59181–84. http://dx.doi.org/10.1039/c6ra10789c.

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28

Nakai, Takeshi, and Koichi Mikami. "[2,3]-Wittig sigmatropic rearrangements in organic synthesis." Chemical Reviews 86, no. 5 (1986): 885–902. http://dx.doi.org/10.1021/cr00075a011.

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29

Leber, Phyllis A., and John E. Baldwin. "Thermal [1,3] Carbon Sigmatropic Rearrangements of Vinylcyclobutanes." Accounts of Chemical Research 35, no. 5 (2002): 279–87. http://dx.doi.org/10.1021/ar010100p.

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30

Davies, Stephen G., A. Christopher Garner, Rebecca L. Nicholson, James Osborne, Edward D. Savory, and Andrew D. Smith. "Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements." Chemical Communications, no. 17 (2003): 2134. http://dx.doi.org/10.1039/b306323m.

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31

ANDREEV, V. G., A. F. KOLOMIETS, and A. V. FOKIN. "ChemInform Abstract: (3,3)Sigmatropic Rearrangements of Fluorocarbanions." ChemInform 24, no. 18 (2010): no. http://dx.doi.org/10.1002/chin.199318109.

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32

Nishibayashi, Yoshiaki, and Sakae Uemura. "ChemInform Abstract: Sigmatropic Rearrangements of Organoselenium Compounds." ChemInform 31, no. 31 (2010): no. http://dx.doi.org/10.1002/chin.200031269.

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33

Barmettler, Peter, and Hans-J�rgen Hansen. "Acid-Catalyzed [3,3]-Sigmatropic Rearrangements ofN-Propargylanilines." Helvetica Chimica Acta 73, no. 6 (1990): 1515–73. http://dx.doi.org/10.1002/hlca.19900730602.

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34

Davies, Stephen G., A. Christopher Garner, Rebecca L. Nicholson, et al. "Doubly diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements." Organic & Biomolecular Chemistry 7, no. 12 (2009): 2604. http://dx.doi.org/10.1039/b902753j.

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35

Onys'ko, P. P., T. V. Kim, E. I. Kiseleva, and A. D. Sinytsa. "Sigmatropic Rearrangements in Phosphorylated 2-Azaallylic Systems." Phosphorus, Sulfur, and Silicon and the Related Elements 49-50, no. 1-4 (1990): 73–76. http://dx.doi.org/10.1080/10426509008038910.

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36

Anderson, James C., Stephen C. Smith, and Martin E. Swarbrick. "Diastereoselective acyclic aza-[2,3] Wittig sigmatropic rearrangements." Journal of the Chemical Society, Perkin Transactions 1, no. 10 (1997): 1517–22. http://dx.doi.org/10.1039/a608226b.

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37

GRIDNEV, I. "Sigmatropic and haptotropic rearrangements in organometallic chemistry." Coordination Chemistry Reviews 252, no. 15-17 (2008): 1798–818. http://dx.doi.org/10.1016/j.ccr.2007.10.021.

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38

Enders, Dieter, Monika Knopp, and Robert Schiffers. "Asymmetric [3.3]-sigmatropic rearrangements in organic synthesis." Tetrahedron: Asymmetry 7, no. 7 (1996): 1847–82. http://dx.doi.org/10.1016/0957-4166(96)00220-0.

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39

Majumdar, K. C., G. H. Jana, S. K. Ghosh, and S. Saha. "Studies on sigmatropic rearrangements: Thermal rearrangement of 3-(meta-substituted aryloxymethyl) coumarins." Monatshefte f�r Chemie Chemical Monthly 128, no. 6-7 (1997): 641–50. http://dx.doi.org/10.1007/bf00807595.

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40

Piers, Edward, Anderson Richard Maxwell, and Neil Moss. "Thermolysis of unsymmetrically substituted vinylcyclopropanes. Regarding the effect of oxygen substituents on the site-selectivity of homo-[1,5]-sigmatropic hydrogen migrations." Canadian Journal of Chemistry 63, no. 2 (1985): 555–57. http://dx.doi.org/10.1139/v85-090.

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Thermal rearrangement of compounds 1, 8–11, and 20 results, in each case, in the exclusive migration of the hydrogen (HΛ) not associated with the oxygen substituent. On the other hand, thermolysis of 19, 22, and 23 provides, in each case, a mixture of the two possible sigmatropic rearrangement products. Similar bond reorganization of the hydrocarbon 21 affords the dienes 27 and 28 (98:2, respectively). On the basis of these results, along with those reported earlier, it is proposed that in the transition states for these rearrangements (a) there is an accumulation of electron density at the carbon from which the hydrogen migrates, and (b) this carbon center has a planar or nearly planar geometry.

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41

Zaim, Ömer. "Rapid [3,3] sigmatropic rearrangements of allylic thiono chloroformates." Tetrahedron Letters 40, no. 46 (1999): 8059–62. http://dx.doi.org/10.1016/s0040-4039(99)01693-7.

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42

Reis, Lucinda V., Ana M. Lobo, and Sundaresan Prabhakar. "Enehydroxylamines as versatile compounds in 3,3-sigmatropic rearrangements." Tetrahedron Letters 35, no. 17 (1994): 2747–50. http://dx.doi.org/10.1016/s0040-4039(00)77022-5.

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43

Gawley, Robert E., and Kwangyul Moon. "Stereoselective [2,3]-Sigmatropic Rearrangements of Unstabilized Nitrogen Ylides†." Organic Letters 9, no. 16 (2007): 3093–96. http://dx.doi.org/10.1021/ol071188v.

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44

Martín-Castro, Ana, and David Serrano-Molina. "Tandem Sequences Involving Michael Additions and Sigmatropic Rearrangements." Synthesis 48, no. 20 (2016): 3459–69. http://dx.doi.org/10.1055/s-0035-1562554.

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45

Stranges, D., P. O’Keeffe, G. Scotti, R. Di Santo, and P. L. Houston. "Competing sigmatropic shift rearrangements in excited allyl radicals." Journal of Chemical Physics 128, no. 15 (2008): 151101. http://dx.doi.org/10.1063/1.2907714.

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46

PURRINGTON, S. T., and S. C. WEEKS. "ChemInform Abstract: (3,3)Sigmatropic Rearrangements of Fluorinated Compounds." ChemInform 24, no. 27 (2010): no. http://dx.doi.org/10.1002/chin.199327320.

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47

Huang, Xueliang, Sebastian Klimczyk, and Nuno Maulide. "ChemInform Abstract: Charge-Accelerated Sulfonium [3,3]-Sigmatropic Rearrangements." ChemInform 43, no. 13 (2012): no. http://dx.doi.org/10.1002/chin.201213249.

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48

Nouri, Dustin H., and Dean J. Tantillo. "Hiscotropic Rearrangements: Hybrids of Electrocyclic and Sigmatropic Reactions." Journal of Organic Chemistry 71, no. 10 (2006): 3686–95. http://dx.doi.org/10.1021/jo052498z.

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49

Pasto, Daniel J., and John E. Brophy. "[1,3]-Hydrogen sigmatropic rearrangements in alkyl-substituted allenes." Journal of Organic Chemistry 56, no. 14 (1991): 4554–56. http://dx.doi.org/10.1021/jo00014a046.

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50

Nguyen, Minh Tho, L. Landuyt, and L. G. Vanquickenborne. "1,3-hydrogen shift in phosphapropenes. Suprafacial sigmatropic rearrangements." Chemical Physics Letters 212, no. 5 (1993): 543–46. http://dx.doi.org/10.1016/0009-2614(93)87242-u.

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