INTERACTION OF 3,4-DIPHENYL-1,2,5-THIADIAZOLE 1,1-DIOXIDE WITH PROTON DONOR SOLVENTS

被引:25
作者
MIRIFICO, MV [1 ]
CARAM, JA [1 ]
VASINI, EJ [1 ]
SICRE, JE [1 ]
机构
[1] NATL UNIV LA PLATA,INIFTA,INST INVEST FISICOQUIM TEORICAS & APLICADAS,RA-1900 LA PLATA,ARGENTINA
关键词
D O I
10.1002/poc.610060605
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The UV spectra of 3,4-diphenyl-1,2,5-thiadiazole 1,1-dioxide (I) and that of its thiadiazoline and thiadiazolidine derivatives were measured in several aprotic and protic solvents. Strong specific interactions of I with protic solvents are observed and the formation of stable carbinolamine type derivatives of I with methanol or ethanol is proposed. Spectroscopic data (UV, H-1 and C-13 NMR) and electrochemical evidence for their formation are given and a new thiadiazoline derivative of I (3-ethoxy-2-methyl-3,4-diphenyl-1,2,5-thiadiazoline 1,1-dioxide) was synthesized. The equilibrium constant for the reaction of 1 with ethanol is reported.
引用
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页码:341 / 346
页数:6
相关论文
共 10 条
[1]   HETEROCYCLES CONTAINING THE SULFAMIDE MOIETY [J].
ARAN, VJ ;
GOYA, P ;
OCHOA, C .
ADVANCES IN HETEROCYCLIC CHEMISTRY, 1988, 44 :81-197
[2]   EMPIRICAL PARAMETERS FOR DONOR AND ACCEPTOR PROPERTIES OF SOLVENTS [J].
GUTMANN, V .
ELECTROCHIMICA ACTA, 1976, 21 (09) :661-670
[3]   CHEMISTRY OF 1,2,5-THIADIAZOLES .3. [1,2,5]THIADIAZOLO[3,4-C][1,2,5]THIADIAZOLE [J].
KOMIN, AP ;
STREET, RW ;
CARMACK, M .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (19) :2749-2752
[4]   HYDROLYSIS OF 3,4-DIPHENYL-1,2,5-THIADIAZOLE-1,1-DIOXIDE - ACID AND BASE CATALYSIS [J].
MIRIFICO, MV ;
VASINI, EJ ;
SICRE, JE .
INTERNATIONAL JOURNAL OF CHEMICAL KINETICS, 1991, 23 (03) :197-202
[5]   ELECTROREDUCTION OF 3,4-DIPHENYL-1,2,5-THIADIAZOLE-1,1-DIOXIDE IN ACETONITRILE SOLUTION AND REACTIONS WITH PROTON DONORS [J].
MIRIFICO, MV ;
CARAM, JA ;
VASINI, EJ .
ELECTROCHIMICA ACTA, 1991, 36 (01) :167-171
[7]  
Riddick J.A., 1970, TECHNIQUES CHEM, V2
[8]  
VOGEL AI, 1948, TXB PRACTICAL ORGANI, P166
[9]  
WEINSTOCK LM, 1984, COMPREHENSIVE HETERO, V6, P514