Tandem Fragmentation of Cyclopropylcarbinyl/Oxiranylcarbinyl Radicals. On the Reversibility of Oxiranylcarbinyl/Allyloxyl Radical Formation

Article abstract of DOI:10.1021/jo00089a012

The tandem radical fragmentation of four stereoisomeric epoxy thiocarbonates 7c-10c has been investigated.In each instance a cyclopropylcarbinyl 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 under acid catalysis.The reversibility of allyloxyl radical formation is considered.