The Journal of Organic Chemistry

Synthesis of haloalkyl esters of trifluoromethanesulfonic acid by the regio-and stereospecific addition of chlorine (I) and bromine (I) trifluoromethanesulfonate to …

Y Katsuhara, DD DesMarteau

Index: Katsuhara, Yutaka; DesMarteau, Darryl D. Journal of Organic Chemistry, 1980 , vol. 45, # 12 p. 2441 - 2446

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Citation Number: 24

Abstract

The synthesis of a variety of haloalkyl esters of trifluoromethanesulfonic acid was achieved by the addition of CF3S020C1 and CF3S020Br to alkenes. Addition to simple alkenes such as CH2= CH2, CF2= CH2, CF2= CF2, CF2== CFCl, CF2= CC12, CHCl= CHCl, and CHF= CHF occur readily at low teperature to give the esters in high yield. With unsymmetrical alkenes, only one structural isomer is observed in every case. With the hypochlorite, cis- ...