tert-Butyl-End-Capped Polyynes: Crystallographic Evidence of Reduced Bond-Length Alternation

被引:86
作者
Chalifoux, Wesley A.
McDonald, Robert [1 ]
Ferguson, Michael J. [1 ]
Tykwinski, Rik R.
机构
[1] Univ Alberta, Dept Chem, X Ray Crystallog Lab, Edmonton, AB T6G 2G2, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
alkynes; carbynes; coupling reactions; polyynes; structure elucidation; SP-CARBON CHAINS; ACETYLENIC-COMPOUNDS; OPTICAL-PROPERTIES; PROTECTIVE METHOD; TERMINAL ALKYNES; SILYLATION; RESEARCHES; OLIGOYNES; EFFICIENT; CHEMISTRY;
D O I
10.1002/anie.200902760
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cumulene or polyyne? The synthesis and X-ray crystallographic analysis of a series of polyynes up to 20 Csp atoms in length and end-capped with tert-butyl groups has been achieved. The structural data show a distinct reduction in the bondlength alternation as a function of the polyyne length, but this trend appears to saturate before a cumulenic-like structure is achieved. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:7915 / 7919
页数:5
相关论文
共 63 条
[1]  
ABOULFADL H, UNPUB
[2]   POLYACETYLENE .4. DARSTELLUNG VON DI-TERT-BUTYL-POLYACETYLENEN [J].
BOHLMANN, F .
CHEMISCHE BERICHTE-RECUEIL, 1953, 86 (05) :657-667
[3]   Submerged electric arc between graphite electrodes: a one-pot tool for the synthesis of long-chain polyynes in solution [J].
Cataldo, F .
TETRAHEDRON LETTERS, 2004, 45 (01) :141-144
[4]  
Cataldo F, 2005, POLYYNES SYNTHESIS P
[5]   Polyyne synthesis using carbene/carbenoid rearrangements [J].
Chalifoux, Wesley A. ;
Tykwinski, Rik R. .
CHEMICAL RECORD, 2006, 6 (04) :169-182
[6]   Synthesis of extended polyynes: Toward carbyne [J].
Chalifoux, Wesley A. ;
Tykwinski, Rik R. .
COMPTES RENDUS CHIMIE, 2009, 12 (3-4) :341-358
[7]   1,4-Bis(triisopropylsilyl)buta-1,3-diyne and 1,4-bis(biphenyl-4-yl)buta-1,3-diyne [J].
Constable, Edwin C. ;
Gusmeroli, Deborah ;
Housecroft, Catherine E. ;
Neuburger, Markus ;
Schaffner, Silvia .
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2006, 62 :O505-O509
[8]   RESEARCHES ON ACETYLENIC COMPOUNDS .39. GENERAL ROUTES TO ALIPHATIC POLYACETYLENIC HYDROCARBONS AND GLYCOLS [J].
COOK, CL ;
JONES, ERH ;
WHITING, MC .
JOURNAL OF THE CHEMICAL SOCIETY, 1952, (JUL) :2883-2891
[9]   sp carbon chains surrounded by sp3 carbon double helices:: Directed syntheses of wirelike Pt(CC)nPt moieties that are spanned by two P(CH2)mP linkages via alkene metathesis [J].
de Quadras, Laura ;
Bauer, Eike B. ;
Mohr, Wolfgang ;
Bohling, James C. ;
Peters, Thomas B. ;
Martin-Alvarez, Jose Miguel ;
Hampel, Frank ;
Gladysz, John A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (26) :8296-8309
[10]   Toward metal-capped one-dimensional carbon allotropes:: Wirelike C6-C20 polyynediyl chains that span two redox-active (η5-C5Me5)Re(NO)(PPh3) endgroups [J].
Dembinski, R ;
Bartik, T ;
Bartik, B ;
Jaeger, M ;
Gladysz, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (05) :810-822