TANDEM FRAGMENTATION OF CYCLOPROPYLCARBINYL OXIRANYLCARBINYL RADICALS- ON THE REVERSIBILITY OF OXIRANYLCARBINYL/ALLYLOXYL RADICAL FORMATION/

Authors
ZIEGLER FE PETERSEN AK
Citation
Fe. Ziegler et Ak. Petersen, TANDEM FRAGMENTATION OF CYCLOPROPYLCARBINYL OXIRANYLCARBINYL RADICALS- ON THE REVERSIBILITY OF OXIRANYLCARBINYL/ALLYLOXYL RADICAL FORMATION/, Journal of organic chemistry, 59(10), 1994, pp. 2707-2714
Citations number
65
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
59
Issue
10
Year of publication
1994
Pages
2707 - 2714
Database
ISI
SICI code
0022-3263(1994)59:10<2707:TFOCOR>2.0.ZU;2-N
Abstract
The tandem radical fragmentation of four stereoisomeric epoxy thiocarb onates 7c-10c has been investigated. In each instance a cyclopropylcar binyl radical fragments to generate an oxiranylcarbinyl radical, which , in turn, undergoes fragmentation. The Initially detected product is (Z)-allylic alcohol 23, which isomerizes to (E)-allylic alcohol 24 und er acid catalysis. The reversibility of allyloxyl radical formation is considered.