Photolysis and Thermal Decay of the Sulfur Dioxide Adducts of Benzobenzvalene
- 1 January 1993
- journal article
- research article
- Published by Taylor & Francis in Phosphorus, Sulfur, and Silicon and the Related Elements
- Vol. 74 (1-4) , 417-418
- https://doi.org/10.1080/10426509308038143
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.Keywords
This publication has 5 references indexed in Scilit:
- A Novel Cycloaddition Reaction of Thermally Generated SulfenesChimia, 1992
- The Photoreversible Addition of Sulfur Dioxide to Benzobenzvalene: A new Approach to the Benzoprefulvene BiradicalHelvetica Chimica Acta, 1990
- Thermal rearrangements of C10H8 species; benzvalene analogs and the automerization of naphthaleneJournal of the American Chemical Society, 1986
- Diazabenzosemibullvalene. A precursor to the benzoprefulvene biradical and indenylmethyleneJournal of the American Chemical Society, 1986
- Die Synthese und der thermische Zerfall des 1,2‐Diazabenzo[e]‐semibullvalens und dessen Beziehung zur Thermolyse des BenzobenzvalensHelvetica Chimica Acta, 1986