Surnmory. When treated with lead tetraacetate, cyclopropylcarbinol and cyclopropylmethylcarbinol do not give @-fragmentation products resulting from the intermediate formation of cyclopropyl radicals; however, cyclopropylmethylcarbinol affords a small amount of a fragmentation product which arises from C,-C/, bond cleavage involving removal of a methyl radical. I n contrast, cyclobutylcarbinol undergoes @-fragmentation in 18% yicld with formation of both the unrearranged cyclobutyl acetate and the rearranged cyclopropylmethyl acetate. These results suggest thc following order of increasing radical stability: cyclopropyl < methyl < cyclobutyl, whereas the isolation of the isomcric fragmentation acetates in the lead tetraacetate rcaction of cyclobutylcarbinol represents further evidence that in the @-fragmentation process the initially produced carbon radical fragment is in major part oxidized to the corresponding carbonium ion before final product formation.
OCOR (IV)c) Cyclopropylc"rbino1, K-C,H,OH ( J ) "j Cycloprop)hnethyl-iormiat, K-CH,OCHO (V) "j C)-clopropylnieth~l-acetat, 11-CH,OCOCH, (Vl) ") Cycloprop?-lriiethyl-ph(~n~l-ather, K-CH, --0 C,H, (VII) ") 1 , 2 , .l-Triacetoxyhutan, AcC)CIi,-C H (0 Ac) -CH, -CH,O Xc ( V I 1 I) ") 1,3-~iacetosy-2-acctox~1nethyl-pl-opan, I\cOCH,-CH(CI-I,O.Ac)-CH,OAc (TX)") -1