Premium
The Photosensitized Oxidation of Strained Olefins
Author(s) -
Frimer Aryeh A.
Publication year - 1981
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198100039
Subject(s) - chemistry , allylic rearrangement , ring strain , olefin fiber , double bond , strain (injury) , ionization , ring (chemistry) , photochemistry , singlet state , ground state , ionization energy , excited state , organic chemistry , atomic physics , catalysis , medicine , ion , physics
The effect of strain in determining the rate, mode and direction of singlet oxygen attack is explored using small ring olefins as substrates. The data suggests that 1 O 2 is relatively insensitive to strain considerations present in either the starting material or the product. More important factors seem to be the ground state geometry of the olefin, the interatomic distance between the α‐olefinic carbon and the γ‐allylic hydrogen, and the ionization potential of the double bond. Strain does, however, play a crucial and fascinating role in the secondary rearrangements of the primary 1 O 2 products.