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Open Access A Novel Cycloaddition Reaction of Thermally Generated Sulfenes

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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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Document Type: Research Article

Publication date: April 1, 1992

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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