PERHALOGENMETHYLMERCAPTO-HETEROCYCLEN, .9. (PERCHLORMETHYLMERCAPTO)PYRIDINE AND (PERFLUORMETHYLMERCAPTO)PYRIDINE

被引:11
作者
HAAS, A
NIEMANN, U
机构
关键词
D O I
10.1016/S0022-1139(00)82464-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Methods of substituting pyridine by perhalogenomethylmercapto groups are discussed. The side chain chlorination of 2-(methylmercapto)pyridine leads gradually to 2-(trichloromethylmercapto)pyridine hydrochloride (1a) and 2-(trichloromethylmercapto)pyridine (1b). Neither a direct reaction of pyridine with CF3SCl nor the way over a Grignard reaction or a sulfenylcarboxylate lead to CF3S-substituted products. Reactions of pyridine and bromopyridines with Hg(SCF3)2 yield 1:1-adducts (2a-d) only. Lithium tetrakis(1,2-dihydro-1-pyridyl)aluminate (LDPA) reacts with CF3SCl to give 3-(trifluoromethylmercapto)pyridine (3); in addition a disubstituted product can be identified massspectroscopically. 1H- and 19F-NMR-spectra are reported. © 1978.
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页码:509 / 518
页数:10
相关论文
共 32 条
[1]  
AHUJA JS, 1970, J CHEM SOC A, P2161
[2]  
ANDREADES S, J ORG CHEM, V29, P898
[3]  
DOWNS AJ, 1961, THESIS U CAMBRIDGE
[4]  
DOYLE P, 1970, TETRAHEDRON LETT, P3371
[5]  
Farbenindustrie I. G., 1937, Fr. Patent, Patent No. [820,796, 820796]
[6]  
Giam C. S., 1969, CHEM COMMUN, P142
[7]   NOVEL SYNTHESIS OF 3-SUBSTITUTED PYRIDINES FROM PYRIDINE [J].
GIAM, CS ;
ABBOTT, SD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (05) :1294-&
[8]  
GIAM CS, 1970, CHEM COMMUN, P478
[9]   DIE REAKTION DES PHENYL-AZO-TRIPHENYLMETHANS MIT PYRIDIN - EIN BEITRAG ZUR FRAGE DER ZWISCHENSTUFE BEI DER RADIKALISCHEN PHENYLIERUNG [J].
GRASHEY, R ;
HUISGEN, R .
CHEMISCHE BERICHTE-RECUEIL, 1959, 92 (10) :2641-2645
[10]  
Gregory W. A., 1956, U.S. Patent, Patent No. [2,763,692, 2763692]