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Volumn 61, Issue 8, 1996, Pages 2813-2825

Substituent effects on rates and stereoselectivities of conrotatory electrocyclic reactions of cyclobutenes. A theoretical study

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Indexed keywords


EID: 0000203981     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo950884i     Document Type: Article
Times cited : (114)

References (42)
  • 15
    • 85033848392 scopus 로고
    • Ph. D. Dissertation, University of California, Los Angeles.
    • (e) Evanseck, J. D. Ph. D. Dissertation, University of California, Los Angeles. 1990.
    • (1990)
    • Evanseck, J.D.1
  • 20
    • 0013203050 scopus 로고
    • de Meijere, A , Blechert, S . Eds.: Kluwer Academic Publishers: Dordrecht
    • Houk, K N in Strain and Its Implications in Organic Chemistry, de Meijere, A , Blechert, S . Eds.: Kluwer Academic Publishers: Dordrecht, 1989, p 25
    • (1989) Strain and Its Implications in Organic Chemistry , pp. 25
    • Houk, K.N.1
  • 21
    • 0346589660 scopus 로고
    • 2, -F, -Me) play no crucial role. He proposes that the σ bond by which these groups are attached is more important in influencing torquoselectivity. Epiotis, N. THEOCHEM 1990, 66, 225
    • (1990) Theochem , vol.66 , pp. 225
    • Epiotis, N.1
  • 27
    • 0000274218 scopus 로고
    • Carpenter predicted that any substituent at the 1-position of cyclobutene should destabilize the transition structure causing an elevation of activation energy and concomitant deceleration of the reaction. However, this prediction was derived from Huckel calculations of Möbius cyclobutadiene as a model of the conrotatory transition structure, which is based on assumption of complete delocalization in the transition state. It does not differentiate the effects we have observed between donor and acceptor substituents. (Carpenter, B. Tetrahedron 1978, 34, 1877).
    • (1978) Tetrahedron , vol.34 , pp. 1877
    • Carpenter, B.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.