Ramberg-Backlund rearrangement vs. β-Elimination of haloform from trichloro and trifluoromethyl sulfones

Samuel Braverman, Yossi Zafrani

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

A new and convenient method for the preparation of trichloro and trifluoromethanesulfinates is described. These esters readily undergo rearrangement to the corresponding sulfones at room temperature, in high yields. In contrast to trichloromethyl sulfoxides which undergo base-induced β-elimination of chloroform to sulfines, the corresponding sulfones undergo an unusually facile Ramberg-Backlund rearrangement with formation of dichloromethylene products. Replacement of CCl3 by CF3 results in complete loss of reactivity, even under drastic basic conditions.

Original languageEnglish
Pages (from-to)1901-1912
Number of pages12
JournalTetrahedron
Volume54
Issue number9
DOIs
StatePublished - 26 Feb 1998

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