Tetrahedron Letters p. 4485 - 4488 (1989)
Update date:2022-07-29
Topics:
Jefford, Charles W.
Velarde, Javier
Bernardinelli, Gerald
Methylene blue-sensitized photo-oxygenation of Z-2-(3'-oxobutyl)methoxymethylidenecyclohexane (7)in CH2Cl2 at -78 deg C, followed by catalysis with Amberlyst-15, gave an epimeric pair of methoxy-1,2,4-trioxanes (9 and 10) and an isomeric peroxide (11) in 67 and 30percent yields.The E-isomer (8) under the same conditions also gave 9-11 (48percent) and 2-formyl-3-(3'-oxobutyl)cyclohexene (30percent).Trioxanes are formed by cyclization of an initially formed 1,2-dioxetane.
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