Journal of the Chemical Society. Chemical communications p. 1480 - 1481 (1986)
Update date:2022-08-18
Topics:
Cavazza, Marino
Pietra, Francesco
Irradiation of 3-methoxycyclopent-2-en-1-one (1) and an excess of acetylene in MeCN at O deg C with Pyrex-filtered light from a Hg-lamp gives 5-methoxycyclohepta-2,4-dien-1-one (2), which undergoes SeO2 oxidation to 4-methoxytropone (3), a known source of γ-tropolone (4); using dideuterioacetylene in place of acetylene, a 3:2 mixture of the isomeric 2,3- and 3,4-dideuterio analogues of (2) is obtained, suggesting a limitation of this method for substituted γ-tropolones.
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