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Sonochemical lactonization of olefins with ceric ammonium nitrate and monomethyl ester of malonic acid

✍ Scribed by Andrea D'Annibale; Corrado Trogolo

Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 222 KB
Volume: 35
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)73056-5

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✦ Synopsis

Abrlrad-Luctonization of okflns wirh monomet&vl ester of makmic a&i and ceric ammonium nittwte was cmried out in acettc octd and in -tawitrile am&r shnple mechanical stirring or vidirradiation Compmvtivensvltrorc yxuted; fw acttmted olrflns a good drtwnic accelemtioa ~45 observed Lactonization of oleks promo&d by Mn(OA& is a widely used methodology of -step synthe& of ylactones.l From a mechanistic point of view, two single dectron tmnsfer (SET) steps are involved (see Scheme 1) i.e. the generation of carboxyalkyl radical (step a) and the oxidation to carbocation of the radicaI &ct formed by addition of the initial radical to olefinic double bond (step b).

Scheme 1

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