Intramolecular cyclization of radicals generated from α-halomethylsulfonamides

被引:21
作者
Leit, SM [1 ]
Paquette, LA [1 ]
机构
[1] Ohio State Univ, Evans Chem Labs, Columbus, OH 43210 USA
关键词
D O I
10.1021/jo991344e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of homologous alpha-sulfonamidyl radicals has been generated by reaction of alpha-halomethyl precursors with tri-n-butyltin hydride under AIBN catalysis. The intramolecular cyclization Capability of these highly reactive intermediates has been evaluated. Where possible, five-membered sultams are formed by 5-exo transition states. The longer C-SO2 and SO2-NR2 bonds have little demonstrable effect on this pathway. In larger systems, however, the 7-endo option predominates over the 6-exo alternative. A preparatively useful route to sultams has emerged from this investigation.
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页码:9225 / 9229
页数:5
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