A TANDEM DENITRATION DEOXYGENATION OF ALPHA-NITRO KETONES VIA (PARA-TOLYLSULFONYL)HYDRAZONES WITH LITHIUM ALUMINUM-HYDRIDE - A PRACTICAL SYNTHESIS OF (Z)-9-TRICOSENE, THE SEX-PHEROMONE OF THE HOUSEFLY (MUSCA-DOMESTICA)

被引:21
作者
BALLINI, R [1 ]
PETRINI, M [1 ]
ROSINI, G [1 ]
机构
[1] UNIV BOLOGNA,DIPARTIMENTO CHIM ORGAN A MANGINI,I-40136 BOLOGNA,ITALY
关键词
D O I
10.1021/jo00304a032
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The utilization of a-nitro ketones in organic synthesis has been increased by the discovery of efficient procedures to affect the substitution of the nitro group with hydrogen or deuterium. Procedures and examples of the utilization of functionalized nitroalkanes as reagents for alkyl anion synthons to build structures in a convenient and predictable way1'2have been reviewed. © 1990, American Chemical Society. All rights reserved.
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页码:5159 / 5161
页数:3
相关论文
共 33 条
[1]   ULTRASOUND IN OXOCHROMIUM(VI) AMINE-MEDIATED OXIDATIONS MODIFICATIONS OF THE COREY-SUGGS OXIDATION FOR THE FACILE CONVERSION OF ALCOHOLS TO CARBONYL-COMPOUNDS [J].
ADAMS, LL ;
LUZZIO, FA .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (22) :5387-5390
[2]   ANODIC SYNTHESES .11. SYNTHESIS OF TARIRIC AND PETROSELINIC ACID [J].
BAKER, BW ;
KIERSTEAD, RW ;
LINSTEAD, RP ;
WEEDON, BCL .
JOURNAL OF THE CHEMICAL SOCIETY, 1954, (JUN) :1804-1808
[3]  
BALLINI R, 1984, ORG PREP P INT, V16, P289
[4]   HYPERCONJUGATION .4. THE BROMINATION OF ADDITIONAL MONOALKYLBENZENES [J].
BERLINER, E ;
BERLINER, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (01) :222-227
[5]   VINYLIC ORGANOBORANES .9. A GENERAL STEREOSPECIFIC SYNTHESIS OF (Z)-DISUBSTITUTED AND (E)-DISUBSTITUTED ALKENES VIA ORGANOBORANES [J].
BROWN, HC ;
BASAVAIAH, D ;
KULKARNI, SU ;
BHAT, NG ;
PRASAD, JVNV .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (02) :239-246
[6]   ALKALI ORGANOMETAL COMPOUNDS .1. THE REACTION OF BENZYLSODIUM WITH ALKYL HALIDES [J].
BRYCESMITH, D ;
TURNER, EE .
JOURNAL OF THE CHEMICAL SOCIETY, 1950, (AUG) :1975-1979
[7]  
Caglioti, 1972, ORG SYNTH, V52, P122
[8]  
CAGLIOTI L, 1964, CHEM IND-LONDON, P153
[9]   REDUCTION OF TOSYLHYDRAZONES AND OF ACYL TOSYLHYDRAZIDES [J].
CAGLIOTI, L .
TETRAHEDRON, 1966, 22 (02) :487-&
[10]   SEX ATTRACTANT PHEROMONE OF HOUSE FLY - ISOLATION, IDENTIFICATION AND SYNTHESIS [J].
CARLSON, DA ;
MAYER, MS ;
SILHACEK, DL ;
JAMES, JD ;
BEROZA, M ;
BIERL, BA .
SCIENCE, 1971, 174 (4004) :76-&