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Photolysis and Thermal Decay of the Sulfur Dioxide Adducts of Benzobenzvalene

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Schmidlin, Serge
Published in Phosphorus, Sulfur, and Silicon and the Related Elements. 1993, vol. 74, no. 1-4, p. 417 - 418
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.
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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. https://archive-ouverte.unige.ch/unige:8460

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Deposited on : 2010-06-25

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