The Journal of organic chemistry

The regiochemistry of cyclization of α-sulfenyl-, α-sulfinyl-, and α-sulfonyl-5-hexenyl radicals: Procedures leading to regioselective syntheses of cyclic sulfones and …

EW Della, SD Graney

Index: Della, Ernest W.; Graney, Sean D. Journal of Organic Chemistry, 2004 , vol. 69, # 11 p. 3824 - 3835

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Citation Number: 21

Abstract

A study of the cyclization of α-sulfenyl-, α-sulfinyl-, and α-sulfonyl-5-hexenyl and 5-methyl-5- hexenyl radicals reveals a unique contrast in the mode of ring closure of the radicals. In the case of the 5-hexenyl radicals, the sulfinyl-substituted species displays unexpected regioselectivity relative to its analogues. Thus, while the α-S-and α-SO2-5-hexenyl radicals give measurable and increasing quantities of 6-endo product, the α-sulfinyl species ...

~73%

~72%

~80%

Organosulfur chemistry. II. Use of dimethyl sulfoxide; A fac...

[Nagasawa, Kazuo; Yoneta, Akemi Chemical & Pharmaceutical Bulletin, 1985 , vol. 33, # 11 p. 5048 - 5052]

The regiochemistry of cyclization of α-sulfenyl-, α-sulfinyl...

[Della, Ernest W.; Graney, Sean D. Organic Letters, 2002 , vol. 4, # 23 p. 4065 - 4067]