Scientific article

The Reaction of Singlet Oxygen with α- and β-Pinenes

Published inHelvetica chimica acta, vol. 56, no. 7, p. 2649-2659
Publication date1973-11-07

The reaction of photogenerated singlet oxygen with α- and β-pinenes has been carefully re-examined. α-Pinene almost exclusively (99.3% yield) furnishes trans-3-hydroperoxy-pin2(10)-ene. However, detectable amounts of the three other possible products are also found, viz., cis-3-hydroperoxypin-2 (10)-ene (˜0.8%), and cis- and trans-2-hydroperoxypin-3 (4)-ene (˜0.04%). β-Pinene gives 99.9% of 10-hydroperoxypin-2 (3)-ene and a trace (˜0.01%) of norpinan-2-one. Rates of reaction and product composition are treated by modal analysis and reflect the operation of steric and stereoelectronic factors in a reactant-like transition state.

Citation (ISO format)
JEFFORD, Charles et al. The Reaction of Singlet Oxygen with α- and <i>β</i>-Pinenes. In: Helvetica chimica acta, 1973, vol. 56, n° 7, p. 2649–2659. doi: 10.1002/hlca.19730560748
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Article (Published version)
ISSN of the journal0018-019X

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