AN EFFICIENT SYNTHESIS OF OPEN-CHAIN NITROALCOHOLS BY REGIOSELECTIVE RING-OPENING OF CYCLIC TERT-BETA-NITROALCOHOLS BY SODIUM-BOROHYDRIDE -SHORT SYNTHESIS OF (+ -)-TRIDECAN-12-OLIDE AND (+/-)-9-TETRADECANOLIDE/

Authors
BEZ G SAIKIA AK KALITA D BEZBARUA MS BARUA NC
Citation
G. Bez et al., AN EFFICIENT SYNTHESIS OF OPEN-CHAIN NITROALCOHOLS BY REGIOSELECTIVE RING-OPENING OF CYCLIC TERT-BETA-NITROALCOHOLS BY SODIUM-BOROHYDRIDE -SHORT SYNTHESIS OF (+ -)-TRIDECAN-12-OLIDE AND (+/-)-9-TETRADECANOLIDE/, Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 37(4), 1998, pp. 325-330
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry → ACNP
ISSN journal
03764699
Volume
37
Issue
4
Year of publication
1998
Pages
325 - 330
Database
ISI
SICI code
0376-4699(1998)37:4<325:AESOON>2.0.ZU;2-7
Abstract
It has been demonstrated that a wide variety of cyclic tert-beta-nitro alcohols can be efficiently cleaved regioselectively using stoichiomet ric amount of NaBH4 in organic solvents like dry MeOH, Et2O, CH,CN etc . giving open chain secondary nitroalcohols such as RCH(OH)(CH2)(n)CH2 NO2 where R is alkyl, aryl etc. and n=4,5, etc. The utility of this re action has been demonstrated by achieving short syntheses of naturally occurring (+/-)-tridecan-12-olide and (+/-)-9-tetradecanolide.