Crystal clear structural evidence for electron delocalization in 1,2-dihydro-1,2-azaborines

被引：171

作者：

Abbey, Eric R. ^{[1
]}

Zakharov, Lev N. ^{[1
]}

Liu, Shih-Yuan ^{[1
]}

机构：

[1] Univ Oregon, Dept Chem, Eugene, OR 97403 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 23期

关键词：

D O I：

10.1021/ja8024966

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first examples of "pre-aromatic" 1,2-dihydro-1,2- azaborine heterocycles have been structurally characterized, enabling the direct comparison of delocalized bonds of 1,2-dihydro-1,2-azaborines to their corresponding formal double and single bonds in nonaromatic systems. The crystallographic data provide an unprecedented look into the structural changes that occur in six-membered BN-heterocycles on their road to aromaticity, and they establish with little ambiguity that 1,2-dihydro-1,2-azaborines posse ss delocalized structures consistent with aromaticity.

引用

收藏

页码：7250 / +

页数：4

相关论文

共 41 条

[1] TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS [J].

ALLEN, FH ;

KENNARD, O ;

WATSON, DG ;

BRAMMER, L ;

ORPEN, AG ;

TAYLOR, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12) :S1-S19

[2] Synthesis and coordination chemistry of 3a,7a-azaborindenyl, a new isoelectronic analogue of the indenyl ligand [J].

Ashe, AJ ;

Yang, H ;

Fang, XD ;

Kampf, JW .

ORGANOMETALLICS, 2002, 21 (22) :4578-4580

[3] Synthesis of 1,2-dihydro-1,2-azaborines and their conversion to tricarbonyl chromium and molybdenum complexes [J].

Ashe, AJ ;

Fang, XD ;

Fang, XG ;

Kampf, JW .

ORGANOMETALLICS, 2001, 20 (25) :5413-5418

[4] A synthesis of aromatic five- and six-membered B-N heterocycles via ring closing metathesis [J].

Ashe, AJ ;

Fang, XD .

ORGANIC LETTERS, 2000, 2 (14) :2089-2091

[5] Aminoboratabenzenes. An evaluation of the exocyclic B-N interaction [J].

Ashe, AJ ;

Kampf, JW ;

Muller, C ;

Schneider, M .

ORGANOMETALLICS, 1996, 15 (01) :387-393

[6]

Astruc D., 2002, Modern arene chemistry: Concepts, synthesis, and applications, P1

[7] 10a-Aza-10b-borapyrenes: Heterocyclic analogues of pyrene with internalized BN moieties [J].

Bosdet, Michael J. D. ;

Piers, Warren E. ;

Sorensen, Ted S. ;

Parvez, Masood .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (26) :4940-4943

[8] Blue fluorescent 4a-aza-4b-boraphenanthrenes [J].

Bosdet, Michael J. D. ;

Jaska, Cory A. ;

Piers, Warren E. ;

Sorensen, Ted S. ;

Parvez, Masood .

ORGANIC LETTERS, 2007, 9 (07) :1395-1398

[9]

Brown RCD, 2006, HETEROCYCLES, V70, P705

[10] NEW HETEROAROMATIC COMPOUNDS .26. SYNTHESIS OF BORAZARENES [J].

DAVIES, KM ;

DEWAR, MJS ;

RONA, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (24) :6294-&

← 1 2 3 4 5 →