Anusorn Vorasingha. Chemistry of radicals derived from the fragmentation of cyclobutane ring. Master's Degree(Organic Chemistry). Mahidol University. Mahidol University Library and Knowledge Center. : Mahidol University, 1996.
Chemistry of radicals derived from the fragmentation of cyclobutane ring
Abstract:
It was found that the cyclobutyl carbinyl radical A could be generated by the reaction as shown in scheme I. (Organic Chemistry Formula) The reaction of 1-(1-bromo-1-phenylsulfonylmethyl)cyclobutanol with n-tribu tyltinhydride (n-Bu(,3)SnH) and a,(...)-azoisobutylronitrile (AIBN) in refluxing dry benzene gave the radical A, which fragmented to the acyclic radical B and then trapped by electrophile to give the adduct C. The 1-(1-chloro-1-phenylsulfonylmethyl)cyclobutanol gave 49% yield of the fragmented adduct D, 1-(1-bromo-1-phenylsulfonylmethyl)cyclobutanol gave a higher yield of fragmented adduct D than the former (55% yield), and 1-(1-iodo-1phenylsulfonylmethyl)cyclobutanol gave an unidentified product. (Organic Chemistry Formula) The sequence of reactions provided a novel method for the generation of a d(5) radical species. 1-(1-chloro-1-phenylsulfonylmethyl)cyclobutanol, 1-(1-bromo-1-phenylsul fonylmethyl)cyclobutanol and 1-(1-iodo-1-phenylsulfonylmethyl)cyclobutanol were synthesized in high yield by the reaction of the corresponding lithiohalomethylphenyl sulfone with cyclobutanone as shown in equation II. Equation I