Oxidation of bicyclic monoterpene ketones with Caro's acid.

Ishmuratov, G.; Vydrina, V.; Yakovleva, M.; Galkina, Yu.; Lobko, I.; Muslukhov, R.; Vyrypaev, E.; Tolstikov, A.

Previously unknown seven-membered lactones, (1 R,1′ R,5 S,5′ S)-5,5′-oxybis(1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-one), 2,2-dimethyl-1,6-dioxaspiro[2.6]nonan-7-one, 4-(1-hydroxy-1-methylethyl)-7-methyloxepan-2-one, and (4 R,4′ R,7 S,7′ S)-4,4′-[oxybis(propane-2,2-diyl)]bis(7-methyloxepan-2-one), were synthesized by the Baeyer-Villiger reaction using Caro's acid as a result of oxidative and skeletal transformations of bicyclic monoterpene ketones, ( )-camphor, ( )-nopinone, and (−)-isocaranone.

OXIDATION; KETONES; LACTONES; CHEMICAL synthesis; BAEYER-Villiger rearrangement; CHEMICAL reactions

Russian Journal of Organic Chemistry, 2012, Vol 48, Issue 9, p1210

1070-4280

Academic Journal

10.1134/S1070428012090102