The first example of 2,2-dilithiocyanocyclopropanes:: generation from 2-bromo-2-sulfinylcyanocyclopropanes with tert-butyllithium, property, and a synthesis of fully substituted cyanocyclopropanes

被引：4

作者：

Fukushima, Iori ^{[1
]}

Gouda, Youhei ^{[1
]}

Satoh, Tsuyoshi ^{[1
]}

机构：

[1] Tokyo Univ Sci, Dept Chem, Fac Sci, Shinjuku Ku, Tokyo 1620826, Japan

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 10期

关键词：

geminal dianion; 1,1-dilithiocyclopropane; cyanocyclopropane; sulfoxide-lithium exchange; bromine-lithium exchange;

D O I：

10.1016/j.tetlet.2006.12.148

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,2-Dilithiocyanocyclopropanes were easily generated from 2-bromo-2-(p-tolylsulfinyl)cyanocyclopropanes with tertbutyllithium in toluene at -78 degrees C through concomitant sulfoxide-lithium and bromine-lithium exchange reactions. The gem-di-anions were found to be stable at -78 degrees C for at least 30 min. Reaction of the gem-dianions with electrophiles gave fully substituted cyanocyclopropanes in moderate yields. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：1855 / 1858

页数：4

共 25 条

[1]

BUNCEL E, 1984, COMPREHENSIVE CARBAN

[2] Functionalized organolithium compounds in total synthesis [J].

Chinchilla, R ;

Nájera, C ;

Yus, M .

TETRAHEDRON, 2005, 61 (13) :3139-3176

[3]

Clayden J., 2002, ORGANOLITHIUMS SELEC

[4] STABILIZATION OF PLANAR TETRACOORDINATE CARBON [J].

COLLINS, JB ;

DILL, JD ;

JEMMIS, ED ;

APELOIG, Y ;

SCHLEYER, PV ;

SEEGER, R ;

POPLE, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (18) :5419-5427

[5] CC TRIPLE-BOND STABILIZATION IN 3-MEMBERED RING COMPOUNDS - BORIRYNE, DILITHIUMCYCLOPROPYNE AND BERYLLIRYNE [J].

FRENKING, G .

CHEMICAL PHYSICS LETTERS, 1984, 111 (06) :529-532

[6] Generation and reactivity of α-metalated vinyl ethers [J].

Friesen, RW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (17) :1969-2001

[7]

HASSNER A, 2002, ORGANIC SYNTHESIS BA

[8] The synthesis of enantiomerically pure 4-substituted [2.2]paracyclophane derivatives by sulfoxide-metal exchange [J].

Hitchcock, PB ;

Rowlands, GJ ;

Parmar, R .

CHEMICAL COMMUNICATIONS, 2005, (33) :4219-4221

[9] The generation and reactions of non-stabilized α-aminocarbanions [J].

Katritzky, AR ;

Qi, M .

TETRAHEDRON, 1998, 54 (12) :2647-2668

[10] SYNTHESIS OF 1,1-DILITHIO-2,2,3,3-TETRAMETHYLCYCLOPROPANE [J].

KAWA, H ;

MANLEY, BC ;

LAGOW, RJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (18) :5313-5314

← 1 2 3 →