A convenient synthesis of the flavor and scent material (±)-γ-(Z)-6-dodecenolactone and some analogs via N-chloroamide thermolysis

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Abstract
[Dihydro-5-[Z)-2''-octenyl]-2(3H)-furanone (''.gamma.-(Z)-6-dodecenolactone''), and the sidechain saturated derivative (.gamma.-dodecanolactone), are 2 odiferously interesting natural products which the authors needed in connection with studies of olfaction in animal behavior]. N-Chloro-N-propyl-threo-6,7-dibromododecanamide, prepared by the successive bromination and N-chlorination of N-propyl-(Z)-6-dodecenamide, was subjected to thermolytic homolysis in aqueous dioxane to yield a mixture of products from which, after Zn debromination, .gamma.-6-(Z)-dodecenolactone was isolated. Some analogs of this lactone were similarly prepared.

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