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Scientific article
English

Photolysis and Thermal Decay of the Sulfur Dioxide Adducts of Benzobenzvalene

Contributors

Burger, Ulrich; Schmidlin, Serge; Mareda, Jiri

Published in

Phosphorus, sulfur, and silicon and the related elements, vol. 74, no. 1-4, p. 417-418

Publication date

1993

Abstract

Benzobenzvalene 1 is shown to add SO2 with formation of a strained sulfone 2 and an isomeric γ-sultine 3. Photochemically (254 nm) the two adducts interconvert. Moreover, SO2 is extruded during the irradiation of 2 or 3 with regeneration of 1 and formation of naphthalene. This result is interpreted in terms of a reversible homolytic cleavage leading to an intermediate sulfinyloxy biradical 5 and subsequent formation of the benzoprefulvene biradical 6. The pyrolysis of 2 and 3 gives, in the gas phase (FVP) and in solution, 1H-indene-1-carboxaldehyde 8 and naphthalene. The key step of this thermal reaction is shown to consist of a cycloreversion giving an intermediate sulfene 9. This can be trapped with N-phenyl maleimide (NPMI). Key structures are ascertained by X-ray analysis.

UNIGE affiliation entities

Citation (ISO format)

BURGER, Ulrich, SCHMIDLIN, Serge, MAREDA, Jiri. Photolysis and Thermal Decay of the Sulfur Dioxide Adducts of Benzobenzvalene. In: Phosphorus, sulfur, and silicon and the related elements, 1993, vol. 74, n° 1-4, p. 417–418. doi: 10.1080/10426509308038143

Main files (1)

Article (Published version)

Identifiers

Journal ISSN

1026-7719
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Technical informations

Creation

25/06/2010 14:44:00

First validation

25/06/2010 14:44:00

Update

14/03/2023 15:49:25

Status update

14/03/2023 15:49:25

Last indexation

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