THE EPIMERIZATION OF ALPHA-CHIRAL HYDRAZONES - MENTHONETOSYLHYDRAZONE

被引:11
作者
GARNER, CM
MOSSMAN, BC
PRINCE, ME
机构
[1] Department of Chemistry, Baylor University, Waco
关键词
D O I
10.1016/S0040-4039(00)79327-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first preparation of (-)-menthonetosylhydrazone (2) in diastereomerically pure form is reported. Kinetic studies show that 2 is far more susceptible to acid-catalyzed epimerization (approximately 150x) than is the parent ketone, (-)-menthone (1), a relationship which has not been generally recognized. Conversion of 2 to 1-menthenyllithium (3) using excess butyllithium occurs without detectable epimerization, as determined by analysis of the 1-iodomenthene S obtained by treatment of 3 with iodine in-situ.
引用
收藏
页码:4273 / 4276
页数:4
相关论文
共 27 条
[1]   SYNTHESIS OF A REPRESENTATIVE CIS-TRANS PAIR OF 4,5-DISUBSTITUTED CYCLOPENTENYLLITHIUM REAGENTS [J].
BARTH, W ;
PAQUETTE, LA .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (14) :2438-2443
[2]  
Bergbreiter D.E., 1991, COMPREHENSIVE ORGANI, V2, P503
[3]  
BERGBREITER DE, 1991, COMPHREHENSIVE ORGAN, V8, P327
[4]  
BERGBREITER DE, 1991, COMPHREHENSIVE ORGAN, V6, P776
[5]  
BERGBREITER DE, 1991, COMPHREHENSIVE ORGAN, V8, P939
[6]   SMALL-SCALE PREPARATIVE SEPARATION OF (-)-MENTHONE AND (+)-ISOMENTHONE BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY [J].
BERGMAN, NA ;
HALL, B .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1979, 33 (02) :148-149
[7]   OXIDATION OF SECONDARY ALCOHOLS IN DIETHYL ETHER WITH AQUEOUS CHROMIC ACID - CONVENIENT PROCEDURE FOR PREPARATION OF KETONES IN HIGH EPIMERIC PURITY [J].
BROWN, HC ;
GARG, CP ;
LIU, KT .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (03) :387-&
[8]   RAPID AND UNEQUIVOCAL DETERMINATION OF SYN-ANTI STEREOCHEMISTRY FOR TOLUENESULFONYLHYDRAZONES AND OTHER IMINE DERIVATIVES VIA C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY - SYNTHETIC ADJUNCT [J].
BUNNELL, CA ;
FUCHS, PL .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (15) :2614-2617
[9]   METAL CATALYSIS IN ORGANIC-REACTIONS .9. IRON-INDUCED REACTION OF ORGANO-ALUMINUM COMPOUNDS WITH ALIPHATIC ALK-1-YNES [J].
CAPORUSSO, AM ;
GIACOMELLI, G ;
LARDICCI, L .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (12) :3139-3145
[10]  
Chamberlin A. R., 1990, ORG REACTIONS, V39, P1