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Electron transfer photochemistry of bridged allylcyclopropane systems: novel substitution products via deprotonation
Author(s) -
Zhou Dahui,
Chou Jolene,
Roth Heinz D.
Publication year - 1999
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199912)12:12<867::aid-poc206>3.0.co;2-g
Subject(s) - chemistry , deprotonation , allylic rearrangement , substitution (logic) , substrate (aquarium) , photochemistry , electron transfer , substitution reaction , diene , medicinal chemistry , stereochemistry , organic chemistry , catalysis , computer science , programming language , geology , ion , oceanography , natural rubber
The electron transfer photochemistry of three rigid, bridged allylcyclopropane systems, 3‐carene ( 1 ), tricyclo[4.3.1.0 1,6 ]dec‐3‐ene ( 2 ) and tricyclo[4.4.1.0 1,6 ]undeca‐3,8‐diene ( 3 ), is shown to take an unprecedented course: the major products are novel ‘substitution’ products, in which a hydrogen at an allylic carbon (C 2 ) of the substrate has been replaced by the p ‐cyanophenyl group. Copyright © 1999 John Wiley & Sons, Ltd.