ORGANOBORANES FOR SYNTHESIS .13. SIMPLE, EFFICIENT SYNTHESES OF LONG-CHAIN ALCOHOLS AND CARBOXYLIC-ACIDS

被引：4

作者：

BROWN, HC

IYER, RR

BHAT, NG

RACHERLA, US

BROWN, CA

机构：

[1] H.C. Brown and R.B. Wetherill Laboratories of Chemistry, Purdue University, West Lafayette

来源：

TETRAHEDRON | 1992年 / 48卷 / 42期

关键词：

D O I：

10.1016/S0040-4020(01)85609-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

General, convenient and simple syntheses of long straight chain alcohols and carboxylic acids were developed utilizing organoborane chemistry. One of the methods entails the thermal isomerization of long-chain alkyldicyclohexylboranes, followed by oxidation. An alternative procedure for the preparation of long-chain alcohols involves the KAPA isomerization of internal alkynes to the terminal derivative, followed by dihydroboration with 9-BBN and oxidation. Alternatively, the terminal alkyne can be oxidised directly to the carboxylic acid. In another strategy, the C30-alcohol triacontanol was prepared by employing high pressure carbonylation of a borane intermediate.

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页码：9187 / 9194

页数：8

相关论文

共 39 条

[1] NATURAL FATS AND OILS - RENEWABLE RAW-MATERIALS FOR THE CHEMICAL-INDUSTRY [J].

BAUMANN, H ;

BUHLER, M ;

FOCHEM, H ;

HIRSINGER, F ;

ZOEBELEIN, H ;

FALBE, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (01) :41-62

[2]

BHALERAO UT, 1984, TETRAHEDRON LETT, P5439

[3] POTASSIUM HYDRIDE, A HIGHLY ACTIVE NEW HYDRIDE REAGENT - REACTIVITY, APPLICATIONS, AND TECHNIQUES IN ORGANIC AND ORGANOMETALLIC REACTIONS [J].

BROWN, CA .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (26) :3913-3918

[4] SALINE HYDRIDES AND SUPERBASES IN ORGANIC REACTIONS .9. ACETYLENE ZIPPER - EXCEPTIONALLY FACILE CONTRATHERMODYNAMIC MULTIPOSITIONAL ISOMERIZATION OF ALKYNES WITH POTASSIUM 3-AMINOPROPYLAMIDE [J].

BROWN, CA ;

YAMASHITA, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (04) :891-892

[5] UNUSUALLY SLOW THERMAL-ISOMERIZATION OF ALKYLDIHALOBORANES - A HIGHLY REGIOSPECIFIC AND STEREOSPECIFIC SYNTHESIS OF ALKYLDIHALOBORANES FROM LABILE OLEFINIC STRUCTURES [J].

BROWN, HC ;

RACHERLA, US .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (08) :1389-1391

[6] A REMARKABLE REVERSAL IN THE DIRECTION OF BORON MIGRATION IN THE THERMAL-ISOMERIZATION OF ORGANOBORANES DERIVED FROM 2-METHYL-2-BUTENE [J].

BROWN, HC ;

RACHERLA, US .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (21) :6506-6508

[7] HYDROBORATION .50. HYDROBORATION OF REPRESENTATIVE ALKYNES WITH 9-BORABICYCLO[3.3.1]NONANE - SIMPLE SYNTHESIS OF VERSATILE VINYL BORA AND GEM-DIBORA INTERMEDIATES [J].

BROWN, HC ;

SCOUTEN, CG ;

LIOTTA, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (01) :96-99

[8] ADDITION-COMPOUNDS OF ALKALI-METAL HYDRIDES .23. PREPARATION OF POTASSIUM TRIISOPROPOXYBOROHYDRIDE IN IMPROVED PURITY [J].

BROWN, HC ;

NAZER, B ;

SIKORSKI, JA .

ORGANOMETALLICS, 1983, 2 (05) :634-637

[9] HYDROBORATION .59. THEXYLCHLOROBORANE-METHYL SULFIDE - A NEW STABLE MONOHYDROBORATING AGENT WITH EXCEPTIONAL REGIOSELECTIVITY [J].

BROWN, HC ;

SIKORSKI, JA ;

KULKARNI, SU ;

LEE, HD .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (05) :863-872

[10] CARBONYLATION OF THEXYLDIALKYLBORANES . A NEW GENERAL SYNTHESIS OF KETONES [J].

BROWN, HC ;

NEGISHI, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (20) :5285-&

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