EFFICIENT SYNTHESIS OF BENZYLPHOSPHINE OXIDES AND E-STILBENES

被引：21

作者：

BROWN, KM

LAWRENCE, NJ

LIDDLE, J

MUHAMMAD, F

JACKSON, DA

机构：

[1] UNIV MANCHESTER,INST SCI & TECHNOL,DEPT CHEM,MANCHESTER M60 1QD,LANCS,ENGLAND

[2] ZENECA FINE MFG ORG,N ENGLAND WORKS,HUDDERSFIELD HD2 1FF,W YORKSHIRE,ENGLAND

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 36期

关键词：

D O I：

10.1016/S0040-4039(00)73481-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of substituted benzylphosphine oxides has been synthesised by reduction of the corresponding (alpha-chlorobenzyl)phosphine oxide, derived from the benzaldehyde and chlorodiphenylphosphine, with either sodium borohydride (DMSO, 60-70 degrees C, 12 h) or tributyltin hydride and AIBN (C6H6. 80 degrees C, 2 h). Reaction of the (alpha-lithiobenzyl)phosphine oxide with aldehydes gave exclusively E-alkenes.

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页码：6733 / 6736

页数：4

相关论文

共 18 条

[1] LITHIUM DIPHENYLPHOSPHIDE - CONVENIENT SOURCE AND SOME REACTIONS [J].

AGUIAR, AM ;

MILLS, A ;

BEISLER, J .

JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (03) :1001-&

[2] REDUCTION OF ORGANIC HALOGEN COMPOUNDS BY SODIUM BOROHYDRIDE [J].

BELL, HM ;

VANDERSL.CW ;

SPEHAR, A .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (12) :3923-&

[3] ON THE PREPARATION OF (E)-STILBENE AND (Z)-STILBENE FROM THE DIASTEREOISOMERIC 1,2-DIPHENYL-2-DIPHENYLPHOSPHINOYLETHAN-1-OLS [J].

BUSS, AD ;

WARREN, S ;

LEAKE, JS ;

WHITHAM, GH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (09) :2215-2218

[4]

CARDONA L, 1985, CHEM IND-LONDON, P759

[5] ISOFLAVANS AND A STILBENE FROM WOOD OF THE DECAY-RESISTANT TROPICAL TREE DIPHYSA-ROBINIOIDES [J].

CASTRO, O ;

LOPEZ, J ;

VERGARA, A ;

STERMITZ, FR ;

GARDNER, DR .

JOURNAL OF NATURAL PRODUCTS, 1986, 49 (04) :680-683

[6] REGIOSPECIFIC SYNTHESIS OF (E) UNSATURATED 3,5-DIALKYL-ISOXAZOLES AND DERIVED LEUKOTRIENE ANALOGS USING PHOSPHINE OXIDES [J].

COLLINGTON, EW ;

KNIGHT, JG ;

WALLIS, CJ ;

WARREN, S .

TETRAHEDRON LETTERS, 1989, 30 (07) :877-880

[7] REACTIONS OF CARBONYL-COMPOUNDS WITH TERVALENT PHOSPHORUS REAGENTS .10. MONOCHLOROPHOSPHINES AND ALDEHYDES [J].

DEATH, NJ ;

MILLER, JA ;

NUNN, MJ ;

STEWART, D .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (03) :776-784

[8] Influence of poles and polar linkings on the course pursued by elimination reactions Part V The mechanism of thermal decomposition of quaternary phosphonium hydroxides [J].

Fenton, GW ;

Ingold, CK .

JOURNAL OF THE CHEMICAL SOCIETY, 1929, :2342-2357

[9] USE OF POTATO DISK AND BRINE SHRIMP BIOASSAYS TO DETECT ACTIVITY AND ISOLATE PICEATANNOL AS THE ANTILEUKEMIC PRINCIPLE FROM THE SEEDS OF EUPHORBIA-LAGASCAE [J].

FERRIGNI, NR ;

MCLAUGHLIN, JL ;

POWELL, RG ;

SMITH, CR .

JOURNAL OF NATURAL PRODUCTS, 1984, 47 (02) :347-352

[10] 3,3',5'-TRI-0-METHYLPICEATANNOL AND 4,3',5'-TRI-0-METHYLPICEATANNOL - IMPROVEMENTS OVER PICEATANNOL IN BIOACTIVITY [J].

GILL, MT ;

BAJAJ, R ;

CHANG, CJ ;

NICHOLS, DE ;

MCLAUGHLIN, JL .

JOURNAL OF NATURAL PRODUCTS, 1987, 50 (01) :36-40