Unusual cyclization products derived from photolysis of Breslow's steroidal benzophenone esters

Journal of Organic Chemistry

Volumn 64, Issue 20, 1999, Pages 7651-7653

  Jung, Michael E ^a   Johnson, Ted W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOPHENONE DERIVATIVE; STEROID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PHOTOLYSIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033214881     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990800w     Document Type: Article

References (15)

1. Saul Winstein Fellow, UCLA, 1998-9; Dissertation Award Fellow, UCLA, 1998-9.
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10. 9 We have no good argument for why the primary radical β to silicon (e.g., abstraction of a hydrogen atom from the tert-butyl group) II is formed rather than the corresponding primary radical α to the silicon atom (e.g., abstraction of a hydrogen atom from the methyl group). One possible explanation is that the transition state for abstraction of the hydrogen atom from the methyl group a to silicon suffers from larger steric interactions than the corresponding transition state for abstraction of the hydrogen atom β to the silicon.
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15. Jung, M. E.; Johnson, T. W. Submitted for publication.