Pummerer reactions of N-acetyliminodialkylsulfuranes

✍ Scribed by Hideo Kise; Graham F. Whitfield; Daniel Swern

• Book ID: 104248496
• Publisher: Elsevier Science
• Year: 1971
• Tongue: French
• Weight: 158 KB
• Volume: 12
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)97629-4

✦ Synopsis

In the classical Pummerer reaction, sulfoxides are converted to o-substituted sulfides by acids, anhydrides and acyl bond in sulfoxides (&) and that iminosulfuranes might first examples of Pummerer halides.2 The close formal resemblance in polarity between the S-C the S-N bond in iminosulfuranes (sulfilimines) (3 suggested to us undergo Pummerer-type rearrangements. In this paper we describe the rearrangements involving iminosulfuranes and electrophiles.

N-Acetyliminodimethylsulfurane

(2) was selected as the model compound for a study of the reactions with acetyl chloride, bensoyl chloride, and acetic anhydride, as this ylid is readily prepared in high purity.

3 The results obtained are shown in Table 1.