Generation of synthetic equivalents of benzdiynes from benzobisoxadisiloles

被引:56
作者
Chen, YL
Sun, JQ
Wei, X
Wong, WY
Lee, AWM [1 ]
机构
[1] Hong Kong Baptist Coll, Dept Chem, Ctr Adv Luminescence Mat, Kowloon, Hong Kong, Peoples R China
[2] Hong Kong Baptist Coll, Cent Lab, Inst Mol Technol Drug Discovery & Synth, Kowloon, Hong Kong, Peoples R China
关键词
D O I
10.1021/jo049091z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Linear and angular benzobisoxadisiloles 14 and 16 can serve as the precursors for stepwise generations of the syntetic equivalents of 1,4- and 1,3-benzdiynes. Benzynes generated were trapped as [4+2] cycloaddition products. Two identical or different rings can be fused to the benzdiyne equivalents. Highly substituted arenes were obtained by removing the oxygen bridges from the furan adducts. The synthesis of naphthoxadisilole 28, which can serve as the precursor of 2,3-naphthyne, is also described.
引用
收藏
页码:7190 / 7197
页数:8
相关论文
共 46 条
[41]   The behaviour of non-aromatic halogenides and aether against phenyl lithium [J].
Wittig, G ;
Harborth, G .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1944, 77 (05) :306-314
[42]   Synthetic applications of 3,4-bis(trimethylsilyl)thiophene: Unsymmetrically 3,4-disubstituted thiophenes and 3,4-didehydrothiophene [J].
Ye, XS ;
Wong, HNC .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) :1940-1954
[43]   3,4-Didehydrothiophene: Generation, trapping reactions, and ab initio study [J].
Ye, XS ;
Li, WK ;
Wong, HNC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (10) :2511-2512
[44]   5,6-bis(trimethyl silyl)benzo[c]furan:: a versatile building block for linear polycyclic aromatic compounds [J].
Yick, CY ;
Chan, SH ;
Wong, HNC .
TETRAHEDRON LETTERS, 2000, 41 (31) :5957-5961
[45]   Palladium-catalyzed controlled carbopalladation of benzyne [J].
Yoshikawa, E ;
Radhakrishnan, KV ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (30) :7280-7286
[46]  
ZAHRADNIK R, 1994, J MOL STRUC-THEOCHEM, V119, P335, DOI 10.1016/0166-1280(94)85015-1