aKazan State Medical University, Kazan, Russian Federation bFSUE 'Antidope Centre', Moscow, Russian Federation cDivision of Informational Technologies, Kazan Scientific Centre of the Russian Academy of Sciences, Kazan, Russian Federation
Abstract:
By the reactions of 3-methylcyclopropene-3-carbonitrile with methylenecyclohexane, α-methylstyrene and β-pinene products of their cyclopropanation have been obtained, the formation of the latter proceeding by the Alder-ene addition scheme. A DFT study of the reaction mechanism shows that most favourable are exo transition states with syn configuration of the CN group and the ene moiety.
Document Type:
Article
Language: English
Citation:
R. V. Ashirov, S. A. Appolonova, G. A. Shamov, V. V. Plemenkov, “3-Methylcyclopropene-3-carbonitrile as a new enophile of the Alder-ene reaction”, Mendeleev Commun., 16:5 (2006), 276–278
Linking options:
https://www.mathnet.ru/eng/mendc3622
https://www.mathnet.ru/eng/mendc/v16/i5/p276
This publication is cited in the following 7 articles:
Chunhui Shan, Kangbao Zhong, Xiaotian Qi, Dongdong Xu, Ling-Bo Qu, Ruopeng Bai, Yu Lan, “Long distance unconjugated agostic-assisted 1,5-H shift in a Ru-mediated Alder-ene type reaction: mechanism and stereoselectivity”, Org. Chem. Front., 5:21 (2018), 3178
Rui Jin, Song Liu, Yu Lan, “Distortion–interaction analysis along the reaction pathway to reveal the reactivity of the Alder-ene reaction of enes”, RSC Adv., 5:75 (2015), 61426
T.J.J. Müller, Comprehensive Organic Synthesis II, 2014, 1
Comprehensive Organic Name Reactions and Reagents, 2010, 37
O. A. Lodochnikova, R. V. Ashirov, S. A. Appolonova, I. A. Litvinov, V. V. Plemenkov, “1-Methylcycloprop-2-ene-1-carbonitrile in tandem alder-ene and diels-alder reactions”, Russ J Org Chem, 46:1 (2010), 49
Roman V. Ashirov, Grigory A. Shamov, Olga A. Lodochnikova, I. A. Litvynov, Svetlana A. Appolonova, Vitaly V. Plemenkov, “Tetramerization of 3-Methyl-cyclopropene-3-carbonitrile: A Novel CN-Alder-ene Reaction”, J. Org. Chem., 73:15 (2008), 5985
Roman V. Ashirov, Svetlana A. Appolonova, Grigory A. Shamov, Vitaly V. Plemenkov, “3‐Methylcyclopropene‐3‐carbonitrile as a New Enophile of the Alder‐ene Reaction.”, ChemInform, 38:9 (2007)
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