TELLURIUM-MEDIATED HALOGEN TRANSFER FROM POLYHALOALKANES TO DIYNE ACCEPTORS

被引:39
作者
BLUM, J [1 ]
BAIDOSSI, W [1 ]
BADRIEH, Y [1 ]
HOFFMAN, RE [1 ]
机构
[1] TECH UNIV BERLIN,INST ANORGAN & ANALYT CHEM,D-10623 BERLIN,GERMANY
关键词
D O I
10.1021/jo00120a015
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Elemental tellurium catalyzes transfer of halogen from (CHCl2)(2), from C2HCl5 and from (CHBr2)(2), to the phenylated diynes 1-3, 17, 20, and 24, in which the alkyne moieties are in close proximity. The process is associated with cyclorearrangement reactions by which halogenated polycycles are formed. In boiling C2HCl5, derivatives of 1,2-bis(phenylethynyl)benzenes afford 5-halogenated indeno[2,1-a]indenes, 1,8-bis(phenylethynyl)naphthalene gives a chlorinated benzo[k]fluoranthene derivative, and 2,2'-bis(phenylethynyl)[1,1'-biphenyl] forms 9-chloro-14-phenylbenz[a,c]anthracene. Diynes 25 and 26 in which the ethynyl functions are further removed from each other fail to yield halogenated products. Diyne 25 undergoes oxidative cyclization by which 1,3-diphenyldibenzo[3,4:6,7]cyclohepta[1,2-c]furan (29) is formed. Compound 26 is transformed to hydrocarbon 32, which involves a phenyl ring walk and elimination of H2Te.
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页码:4738 / 4742
页数:5
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