PREPARATION, STRUCTURE, AND REACTIVITY OF 1,3,4-TRIPHENYL-4,5-DIHYDRO-1H-1,2,4-TRIAZOL-5-YLIDENE, A NEW STABLE CARBENE

被引：498

作者：

ENDERS, D ^{[1
]}

BREUER, K ^{[1
]}

RAABE, G ^{[1
]}

RUNSINK, J ^{[1
]}

TELES, JH ^{[1
]}

MELDER, JP ^{[1
]}

EBEL, K ^{[1
]}

BRODE, S ^{[1
]}

机构：

[1] BASF AG,AMMONIAKLAB,D-67056 LUDWIGSHAFEN,GERMANY

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1995年 / 34卷 / 09期

关键词：

CARBENES; CYCLOADDITIONS; HETEROCYCLES; INSERTIONS;

D O I：

10.1002/anie.199510211

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Stable to 150 °C, the heterocyclic carbene 1 is characterized by the typical reactivity of a nucleophilic carbene. Dihydrotriazole 1 can be prepared by simple thermal decomposition of its methanol adduct. X‐ray crystal structure analysis, ab initio calculations, and reactivity studies confirm the nucleophilic carbene character of 1. (Figure Presented.) Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany

引用

收藏

页码：1021 / 1023

页数：3

相关论文

共 38 条

[1] ELECTRON-DISTRIBUTION IN A STABLE CARBENE [J].

ARDUENGO, AJ ;

DIAS, HVR ;

DIXON, DA ;

HARLOW, RL ;

KLOOSTER, WT ;

KOETZLE, TF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) :6812-6822

[2] A STABLE CRYSTALLINE CARBENE [J].

ARDUENGO, AJ ;

HARLOW, RL ;

KLINE, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363

[3] ELECTRONIC STABILIZATION OF NUCLEOPHILIC CARBENES [J].

ARDUENGO, AJ ;

DIAS, HVR ;

HARLOW, RL ;

KLINE, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5530-5534

[4] SYNTHESIS AND STRUCTURE OF THE 1ST CYCLODIPHOSPHAZENE - DIMERIZATION OF A PHOSPHONITRILE GREATER-THAN-P=N [J].

BACEIREDO, A ;

BERTRAND, G ;

MAJORAL, JP ;

SICARD, G ;

JAUD, J ;

GALY, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (20) :6088-6089

[5] 3-ETHYL-2-TETRAZO-6-X-BENZO[D]THIAZOLINES AND THEIR REACTIVITY - A CONTRIBUTION TO THE CHEMISTRY OF NUCLEOPHILIC CARBENES [J].

BALLI, H ;

GRUNER, H ;

MAUL, R ;

SCHEPP, H .

HELVETICA CHIMICA ACTA, 1981, 64 (03) :648-656

[6] STRUCTURE AND ENERGETICS OF SIMPLE CARBENES CH2, CHF, CHCL, CHBR, CF2, AND CCL2 [J].

BAUSCHLICHER, CW ;

SCHAEFER, HF ;

BAGUS, PS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (22) :7106-7110

[7] PARALLEL DIRECT SCF AND GRADIENT PROGRAM FOR WORKSTATION CLUSTERS [J].

BRODE, S ;

HORN, H ;

EHRIG, M ;

MOLDRUP, D ;

RICE, JE ;

AHLRICHS, R .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1993, 14 (10) :1142-1148

[8] PREPARATION OF STABLE DIVALENT SPECIES RAISES ISSUES OF ELECTRONIC-STRUCTURE [J].

DAGANI, R .

CHEMICAL & ENGINEERING NEWS, 1994, 72 (18) :20-22

[9] SINGLET TRIPLET SPLITTINGS IN CF3-SUBSTITUTED CARBENES [J].

DIXON, DA .

JOURNAL OF PHYSICAL CHEMISTRY, 1986, 90 (01) :54-56

[10] ELECTRONIC-STRUCTURE OF LAMBDA-5-PHOSPHAACETYLENES AND CORRESPONDING TRIPLET METHYLENES [J].

DIXON, DA ;

DOBBS, KD ;

ARDUENGO, AJ ;

BERTRAND, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8782-8785

← 1 2 3 4 →