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A Novel Cycloaddition Reaction of Thermally Generated Sulfenes

Schmidlin, Serge P.
Published in Chimia. 1992, vol. 46, no. 4, p. 111-113
Abstract The highly strained ?-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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BURGER, Ulrich et al. A Novel Cycloaddition Reaction of Thermally Generated Sulfenes. In: Chimia, 1992, vol. 46, n° 4, p. 111-113. https://archive-ouverte.unige.ch/unige:7785

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