Tetrahedron p. 3037 - 3044 (1991)
Update date:2022-08-05
Topics:
Spraul, Martin H.
Nitz, Siegfried
Drawert, Friedrich
The photochemical and thermal behaviour of cyclic olefins like p-mentha-1,3,8-triene (2) and structural related p-mentha-1,3- and -1,4-dienes under the influence of oxygen have been investigated. Dehydration, ring opening, (4+2)-cycloaddition of singlet oxygen1 and dimerization were observed as concurring mechanisms. The photochemical and thermal dehydrogenation of α-terpinene (1), α-phellandrene (3), γ-terpinene (4) and p-mentha-1,3,8-triene (2) leads to p-cymene (5) and p-cymenene (6), respectively. The mechanism of this aromatization reaction will be discussed in this paper.
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