DIRECT C-13-NMR SPECTROSCOPIC OBSERVATION OF CYCLOPROPYLIDENE BROMOLITHIOCARBENOIDS

被引：55

作者：

SEEBACH, D

SIEGEL, H

MULLEN, K

HILTBRUNNER, K

机构：

[1] Laboratorium Für Organische Chemie, Eidgenössischen Technischen Hochschule, Eth-Zentrum, CH-8092

[2] Institut für Organische Chemie der Universität, Köln, D-5000

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 1979年 / 18卷 / 10期

关键词：

D O I：

10.1002/anie.197907841

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The nature of the cabenoid 1‐bromo‐1‐lithiocyclopropanes has been examined with 13C‐labeled compounds at −100°C by 13C‐NMR spectroscopy. The pronounced downfield shifts of the cabenoid C signsl suggest considerable weakening of the CBr bond 1 or even rehybridization 2. Thus a LiBr‐complexed carbene appears more likely than a carbanion derivative. (Figure Presented.) Copyright © 1979 by Verlag Chemie, GmbH, Germany

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页码：784 / 785

页数：2

相关论文

共 22 条

[1] STRUCTURAL STUDIES OF CARBANIONIC SPECIES FORMED FROM PHOSPHONATES - ANIONS OF DIETHYL BENZYL-PHOSPHONATES AND CYANOMETHYLPHOSPHONATES [J].

BOTTINSTRZALKO, T ;

SEYDENPENNE, J ;

POUET, MJ ;

SIMONNIN, MP .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (22) :4346-4351

[2] REACTIONS OF 1-BROMO-1-LITHIOCYCLOPROPANES WITH KETONES AND ALDEHYDES - NEW METHOD OF CONVERTING OLEFINS INTO OXASPIROPENTANES, CYCLOBUTANONES, CYCLOPROPYL KETONES, AND LACTONES [J].

BRAUN, M ;

DAMMANN, R ;

SEEBACH, D .

CHEMISCHE BERICHTE-RECUEIL, 1975, 108 (07) :2368-2390

[3] NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY - C-13 SPECTRA OF SOME CYCLIC ALKYNES, ALLENES, AND ALKENES [J].

CHARRIR, C ;

DORMAN, DE ;

ROBERTS, JD .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (15) :2644-2650

[4] C-13 NMR-STUDY OF STRUCTURE OF SULFUR-STABILIZED CARBANIONS [J].

CHASSAING, G ;

MARQUET, A .

TETRAHEDRON, 1978, 34 (09) :1399-1404

[5] REARRANGEMENT OF BROMOCYCLOPROPYL CARBINOLS TO HOMOALLYLIC DERIVATIVES AND TO CYCLOBUTANONES [J].

DAMMANN, R ;

SEEBACH, D .

CHEMISCHE BERICHTE-RECUEIL, 1979, 112 (06) :2167-2176

[6] CYCLIC ALLENES .2. CONVERSION OF CYCLOPROPYLIDENES TO ALLENES - SIMPLEX-INDO STUDY [J].

DILLON, PW ;

UNDERWOOD, GR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (08) :2435-2446

[7] ON STABILIZING A SINGLET METHYLENE [J].

GLEITER, R ;

HOFFMANN, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) :5457-&

[8] MATRIX REACTIONS OF ALKALI-METAL ATOMS WITH TETRAHALOMETHANES - EVIDENCE FOR A NOVEL CARBENOID [J].

HATZENBUHLER, DA ;

ANDREWS, L ;

CAREY, FA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (01) :187-189

[9]

HIYAMA T, 1979, TETRAHEDRON LETT, P2043

[10] STABLE CARBENOIDS .47. CHEMISTRY OF CARBENOIDS AND OTHER THERMOLABILE ORGANOLITHIUM COMPOUNDS [J].

KOBRICH, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1972, 11 (06) :473-&