Effect of allylic oxygen on the reaction pathways of singlet oxygenation: Selective formation of 1,2-dioxetanes from 1-alkoxymethyl-2-aryl-1-tert-butyl-2-methoxyethylenes

DOI: 10.1016/0040-4039(95)02185-X

Source and publish data:

Tetrahedron Letters p. 397 - 400 (1996)

Update date:2022-08-03

Topics:

Authors:

Matsumoto, Masakatsu

Kobayashi, Hisako

Matsubara, Jyunya

Watanabe, Nobuko

Yamashita, Satoshi

Oguma, Daisuke

Kitano, Yoshikazu

Ikawa, Hiroshi

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Article abstract of DOI:10.1016/0040-4039(95)02185-X

Olefins bearing an allylic oxygen 1 undergo 1,2-addition of singlet oxygen to afford exclusively the corresponding 1,2-dioxetanes 2, whereas their methylene analogues 3 suffer competitively 1,2-addition and ene reaction. The reactivity of 1 preferring 1,2-addition is likely attributed to the steering effect by an allylic oxygen.

Full text of DOI:10.1016/0040-4039(95)02185-X

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