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

✍ Scribed by Charles W. Jefford; André F. Boschung; Robert M. Moriarty; Christian G. Rimbault; Mostyn H. Laffer

Publisher
John Wiley and Sons
Year
1973
Tongue
German
Weight
642 KB
Volume
56
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

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.

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