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Volumn , Issue 3, 2005, Pages 593-599

Carbonyl ylide cycloadditions to C,C-double bonds of methylenecyclopropanes

Author keywords

Bicyclopropylidene; Carbonyl ylides; Dipolar cycloaddition; Methylenecyclopropane; Strained molecules

Indexed keywords

CARBONYL DERIVATIVE; CARBONYL YLIDE; CYCLOPROPANE; METHYLENECYCLOPROPANE; UNCLASSIFIED DRUG;

EID: 14544284597     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400601     Document Type: Article
Times cited : (22)

References (69)
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    • A rather limited number of cycloaddition reactions of carbonyl ylides containing a cyclopropane moiety have been published: a) A. Padwa, E. A. Curtis, V. P. Sandanayaka, J. Org. Chem. 1996, 61, 73-81;
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    • Padwa, A.1    Curtis, E.A.2    Sandanayaka, V.P.3
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    • According to HF/6-31G calculations, the phenyl group of (benzylidene)cyclopropane (2a) in the ground state lies in one plane with the cyclopropane ring, and thus efficiently conjugates with the double bond. The two phenyl groups in (diphenylmethylene)cyclopropane, on the other hand, are rotated by 90° out of the plane of the double bond. This results not only in decreased conjugation, but also in increased unfavorable steric encumbrance and may explain why (diphenylmethylene)cyclopropane did not react with carbonyl ylide 6 at all. GAMESS: M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. J. Su, T. L. Windus, M. Dupuis, J. A. Montgomery, J. Comput. Chem. 1993, 14, 1347-1363.
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    • Schmidt, M.W.1    Baldridge, K.K.2    Boatz, J.A.3    Elbert, S.T.4    Gordon, M.S.5    Jensen, J.H.6    Koseki, S.7    Matsunaga, N.8    Nguyen, K.A.9    Su, S.J.10    Windus, T.L.11    Dupuis, M.12    Montgomery, J.A.13
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    • -3. CCDC-249183 (for endo-10d) and CCDC-249184 (for exo-10d) contain the supplementary crystallographic data for this paper.These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.