157

94A

94A

JOURNAL OF ORGANIC CHEMISTRY

V.59, No.4

(1994)

P.845-849

Pyrolysis,Radical reactions,Carbon-14 studies

Decyl acetate and decene pyrolysis under the same reaction conditions show that formation of the minor products during the pyrolysis of esters occurs by a parallel, and not a secondary,reaction.The radioactivity observed in the CO2 andCO produced during the pyrolysis of 1-hexyl acetate-1-14C and the radioactivity in the methane from the pyrolysis of 1-hexyl acetate-2-14C strongly suggested a radical reaction pathway for the formation of the minor products. Considering the above results together with the radioactivity data of gas samples from the pyrolysis of 1-decyl-1-14C acetate, 1-hexyl-1-14C acetate, and 1-heptadecyl-1-14C acetate leads to the conclusion that the mechanism of pyrolysis of esters may be viewed as a cyclo-DE DN AN mechanism for the formation of the major alkene product and a radical mechanism for the formation of minor products. A useful synthetic procedure for the preparation of high carbon number alkenes (>10) also results from this study.

1376/09

Shahsvary

GN111280