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2005
Halogen compounds
P 0030
Solid-State Chlorodecarboxylation of Mono- and Dicarboxylic Acids with
Pb(OAc)4—MCl System. — Reaction of carboxylic acids (I) with the system
33- 074 the
Pb(O-Ac)4—NH4Cl proceeds smoothly to afford the corresponding halogen compounds (II) as chlorodecarboxylation products. In the case of dicarboxylic acids, the
reaction outcome depends on the chain length between the carboxylate groups and on
the reaction conditions. Dichlorides are achieved in high yields from longer-chain dicarboxylic acids (VI) while the smaller analogues (VIII) give lactones (IX) via cyclization of the intermediate monochlorodecarboxylation products. Mixtures of both products and the monochlorodecarboxylation intermediates are observed when the reaction
mixture is not processed in the vibration mill. — (NIKISHIN, G. I.; SOKOVA, L. L.;
CHIZHOV, A. O.; MAKHAEV, V. D.; KAPUSTINA*, N. I.; Russ. Chem. Bull. 53
(2004) 10, 2200-2204; Zelinsky Inst. Org. Chem., Russ. Acad. Sci., Moscow 117913,
Russia; Eng.) — Mischke
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