Reaction of singlet oxygen with alkenylidenecyclopropanes: Implication for a peroxyallyl intermediate

DOI: 10.1016/S0040-4039(00)88757-2

Source and publish data:

Tetrahedron Letters p. 1173 - 1176 (1990)

Update date:2022-08-05

Topics: Reaction Singlet oxygen Alkenylidenecyclopropanes

Authors:

Akasaka, Takeshi

Misawa, Yoshihisa

Ando, Wataru

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Article abstract of DOI:10.1016/S0040-4039(00)88757-2

Photosensitized oxygenation of adamantenylidenecyciopropanes (1) gave either the corresponding oxetanones (2a-c) or the cyclic ketones (4 and 5) depending on the substituent on the cyclopropane ring in addition to adamantanone. The results are rationalized in terms of initial formation of a perepoxide followed by that of a peroxyallyl intermediate.

Full text of DOI:10.1016/S0040-4039(00)88757-2

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