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Scientific article
English

The Photoreversible Addition of Sulfur Dioxide to Benzobenzvalene: a New Approach to the Benzoprefulvene Biradical

Published inHelvetica Chimica Acta, vol. 73, no. 6, p. 1724-1729
Publication date1990
Abstract

Benzobenzvalene (naphthvalene; 1) is shown to add SO2 to a lateral bicyclobutane bond with formation of a sulfone 2 and a ‘γ-sultine' 3. The structure of the latter is unambiguously established by X-ray diffraction. Both adducts extrude SO2 upon direct photolysis at 254 nm and regenerate 1 accompanied by naphthalene in a 1:3 ratio. This result is interpreted in terms of a reversible homolytic cleavage leading, for both, 2 and 3, to the same sulfinyloxy biradical 5, which by loss of SO2 gives the benzoprefulvene biradical 6. The latter in its singlet state undergoes ring closure to 1, or it opens to give naphthalene.

Funding
  • Swiss National Science Foundation - 20-27665.89
Citation (ISO format)
BURGER, Ulrich et al. The Photoreversible Addition of Sulfur Dioxide to Benzobenzvalene: a New Approach to the Benzoprefulvene Biradical. In: Helvetica Chimica Acta, 1990, vol. 73, n° 6, p. 1724–1729. doi: 10.1002/hlca.19900730617
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ISSN of the journal0018-019X
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