Tetrahedron p. 5051 - 5064 (1988)
Update date:2022-08-02
Topics:
Freeman, Peter K.
Siggel, Lorenz
Chamberlain, Paul H.
Clapp, Gary E.
The irradiation of methyl geranate (3) in ether using 254 nm lamps produces methyl 5-methyl-2-isopropenyl-4-hexenoate (13), 1,6,6-trimethyl-endo-5-carbomethoxybicyclo-<2.1.1>hexane (11), methyl 2-isopropenyl-5-methylcyclopentanecarboxylate (12) and methyl (3Z)-3,7-dimethyl-3,6-octadienoate (14).Photolysis run in water or in ether in the presence of base generates two additional dienes: methyl 3-methylene-7-methyl-6-octaenoate (16) and methyl (3E)-3,7-dimethyl-3,6-octadienoate (17).The photolysis of methyl (2E, 6E)-3,7-dimethyl-2,6-nonadienoate (4a) in ether procedures all Z/E isomers, 4a - 4d.
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