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Abstract

OXIDATIVE FRAGMENTATION OF 1, 5-CYCLOOCTADIENE DERIVATIVE: A NEW ENTRY INTO 16-MEMBERED MACROCYCLE

M. M. V. Ramana*, Shrimant V. Rathod and M.S.Raje.

Abstract

Reformatsky reaction was carried out with cyclohexanone and ethyl bromoacetate to give 1-cyclohexenyl acetate which on LAH reduction gave2-(l-cyclohexenyl) ethanol. 1,5-cyclooctadiene derivative i.e 1,2,3,4,5,6,7,8,9,10,11,12-dodecahydrocycloocta[l,2- a:5,6-a']dibenzene was synthesized by domino intermolecular alkylation and cycloalkylation from 2-(l-cyclohexenyl) ethanol. This on oxidative fragmentation using Ruthenium oxide catalysed periodate oxidation afforded 16-membered cyclictetraketone,macrocycle.

Keywords: 1,5-cyclooctadiene, Oxidative fragmentation, 16- membered macrocycle.


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