Tetrahedron

The photochemistry of methyl geranate, a model chromophore for insect juvenile hormone analogs

PK Freeman, L Siggel, PH Chamberlain, GE Clapp

Index: Freeman, Peter K.; Siggel, Lorenz; Chamberlain, Paul H.; Clapp, Gary E. Tetrahedron, 1988 , vol. 44, # 16 p. 5051 - 5064

Full Text: HTML

Citation Number: 10

Abstract

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-octadlenoate (14). Photolysis run in water or in ether in the presence of base generates two additional dienes: methyl 3-methylene-7-methyl-6-octenoate (16) and ...