A Novel Cycloaddition Reaction of Thermally Generated Sulfenes

Authors

  • Ulrich Burger
  • Serge P. Schmidlin
  • Jiri Mareda
  • Gerald Bernardinelli

DOI:

https://doi.org/10.2533/chimia.1992.111

Abstract

The highly strained γ-sultine 4, resulting from the addition of SO2 to benzobenzvalene, is shown to undergo a thermal cycloreversion which gives 1H-indene-1-thiocarbaldehyde dioxide (6) as an intermediate and subsequently 1H-indene-1-carbaldehyde (5). The sulfene can be intercepted with electron poor C=C bonds in a cycloaddition process leading to a five-membered ring. The structure of the fused heterocyclic product 8b resulting from addition of the sulfene 6 to N-phenyl-maleimide was ascertained by X-ray analysis. Pent-4-enethial dioxide (12) produced by a sulfo-Cope rearrangement from allyl vinyl sulfone (11) is found to add to N-phenylmaleimide in the same 1,3-dipolar fashion as the sulfene 6. The cycloadditions need not be via concerted pathways.

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Published

1992-04-29

How to Cite

[1]
U. Burger, S. P. Schmidlin, J. Mareda, G. Bernardinelli, Chimia 1992, 46, 111, DOI: 10.2533/chimia.1992.111.