Azafulvenium methides: new extended dipolar systems

O.B. Sutcliffe, R.C. Storr, T.L. Gilchrist, P. Rafferty

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

The transient 1-azafulvenium methides 24, 26 and 28 generated by thermal extrusion of sulfur dioxide from pyrrolo[1,2-c][1,3]thiazole 2,2-dioxide 20 (R = Me), 22 and 23 undergo sigmatropic [1,8]H shifts and the 1-acyl derivatives 30 electrocyclise to give novel pyrrolo[1,2-c][1,3]oxazines 32. The analogous 1,2-diazafulvenium methide 36 has been intercepted in [8 + 2] cycloadditions with electron-rich silylated acetylenes to give adducts 37-40. This behaviour is partially explained by Frontier MO theory.
Original languageEnglish
Pages (from-to)1759-1806
Number of pages47
JournalJournal of the Chemical Society, Perkin Transactions 1
Volume2001
Issue number15
DOIs
Publication statusPublished - 2001

Keywords

  • acids
  • azafulvenium methides
  • organic chemistry
  • sulfur dioxide

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