Reaction of carbon monoxide with N-lithioketimines derived by the addition of alkyllithium to ortho-substituted benzonitriles.: Diverse courses of cyclization via carbonyl anions

被引：12

作者：

Kai, H ^{[1
]}

Yamauchi, M ^{[1
]}

Murai, S ^{[1
]}

机构：

[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 565, Japan

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 52期

关键词：

D O I：

10.1016/S0040-4039(97)10412-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Lithioketimines, generated in situ from 2-substituted benzonitriles and t-BuLi, reacted with carbon monoxide to afford five-, six- or seven-membered cyclic products, involving participation by the ortho substituents. The reactions represent new selective transformations of carbonyllithium intermediate which previously were observed to lead to complicated reactions. (C) 1997 Elsevier Science Ltd.

引用

页码：9027 / 9030

页数：4

共 12 条

[1] PROTONATION OF ACYLLITHIUM REAGENTS BY DICHLOROMETHANE AND DICHLOROARYLMETHANE - A NEW METHOD FOR THE SYNTHESIS OF ALPHA,ALPHA-DICHLORO ALCOHOLS [J].

KABALKA, GW ;

LI, NS ;

YU, S .

ORGANOMETALLICS, 1995, 14 (04) :1565-1566

[2] Ynolates from the reaction of lithiosilyldiazomethane with carbon monoxide. New ketenylation reactions [J].

Kai, H ;

Iwamoto, K ;

Chatani, N ;

Murai, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (32) :7634-7635

[3] PROTONATION OF ACYLLITHIUM REAGENTS BY ACETONITRILE - SYNTHESIS OF BETA-HYDROXY NITRILES [J].

LI, NS ;

YU, S ;

KABALKA, GW .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5973-5974

[4] ACYLLITHIUM TO LITHIUM ENOLATE CONVERSION BY A 1,2-SILICON SHIFT - A SHORTCUT TO ACYLSILANE ENOLATES [J].

MURAI, S ;

RYU, I ;

IRIGUCHI, J ;

SONODA, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (08) :2440-2442

[5] ELECTRON-TRANSFER IN THE REACTIONS OF ARYLLITHIUM COMPOUNDS WITH CARBON-MONOXIDE [J].

NUDELMAN, NS ;

DOCTOROVICH, F .

TETRAHEDRON, 1994, 50 (16) :4651-4666

[6] REACTION OF LITHIUM SILYLAMIDES WITH CARBON-MONOXIDE LEADING TO CARBAMOYLSILANES [J].

ORITA, A ;

OHE, K ;

MURAI, S .

ORGANOMETALLICS, 1994, 13 (04) :1533-1536

[7] REACTIONS VIA CARBONYL ANIONS - [4+1] CYCLOCOUPLING OF THE AZADIENYLLITHIUM WITH CARBON-MONOXIDE [J].

ORITA, A ;

FUKUDOME, M ;

OHE, K ;

MURAI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (02) :477-481

[8] INTRAMOLECULAR CONVERSIONS OF ACYLLITHIUM - CYCLIZATION IN THE REACTION OF CARBON-MONOXIDE WITH [1-(SILYL)VINYL]LITHIUM [J].

RYU, I ;

HAYAMA, Y ;

HIRAI, A ;

SONODA, N ;

ORITA, A ;

OHE, K ;

MURAI, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) :7061-7063

[9] Lithium dienolate generation by alpha-regioselective reaction of (1-silylallyl)lithiums with carbon monoxide [J].

Ryu, I ;

Yamamoto, H ;

Sonoda, N ;

Murai, S .

ORGANOMETALLICS, 1996, 15 (26) :5459-5461

[10] HIGH-YIELD ACYL ANION TRAPPING REACTIONS - A SYNTHESIS OF ACYLTRIMETHYLSILANES [J].

SEYFERTH, D ;

WEINSTEIN, RM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (20) :5534-5535

← 1 2 →