Thermolysis of the sulfur dioxide adducts of benzobenzvalene. The 1.3-dipolar behaviour of a sulfene

Burger, Ulrich; Erne-Zellweger, Dominique; Sledeski, Adam W.; Schmidlin, Serge Patrice

doi:10.1016/S0040-4039(00)99128-7

Scientific article

Letter

English

Thermolysis of the sulfur dioxide adducts of benzobenzvalene. The 1.3-dipolar behaviour of a sulfene

ContributorsBurger, Ulrich; Erne-Zellweger, Dominique; Sledeski, Adam W.; Schmidlin, Serge Patrice

Published inTetrahedron Letters, vol. 30, no. 21, p. 2797-2800

Publication date1989

Abstract

Pyrolysis (fvp) of a strained γ-sultine (3) produced 1H-indene-1-carboxaldehyde (8) and naphthalene. The key step in the production of aldehyde (8) involves a 1,3-dipolar cycloreversion, as evidenced by the trapping of an intermediate sulfene (6) with methyl acrylate. A diradical pathway is proposed for the formation of naphthalene.

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Funding

Swiss National Science Foundation - 20-5376.87

Citation (ISO format)

BURGER, Ulrich et al. Thermolysis of the sulfur dioxide adducts of benzobenzvalene. The 1.3-dipolar behaviour of a sulfene. In: Tetrahedron Letters, 1989, vol. 30, n° 21, p. 2797–2800. doi: 10.1016/S0040-4039(00)99128-7

Article (Published version)

Identifiers

PID : unige:152736
DOI : 10.1016/S0040-4039(00)99128-7

Commercial URLhttps://linkinghub.elsevier.com/retrieve/pii/S0040403900991287

Journal ISSN0040-4039

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Thermolysis of the sulfur dioxide adducts of benzobenzvalene. The 1.3-dipolar behaviour of a sulfene

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