RING-CHAIN TAUTOMERISM IN 1,3-THIAZOLIDINES

被引:73
作者
FULOP, F [1 ]
MATTINEN, J [1 ]
PIHLAJA, K [1 ]
机构
[1] UNIV TURKU,DEPT CHEM,SF-20500 TURKU 50,FINLAND
关键词
D O I
10.1016/S0040-4020(01)96019-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
NMR spectroscopy was applied to study ring-chain tautomeric equilibria in several substituted 1,3-thiazolidines. The system highly prefers the ring form and only in the case of 2-(2'-hydroxy,5'-bromophenyl)-l,3-benzothiazo-line (2d) 1H and 13C NMR spectra revealed a detectable amount of the openchain tautomer. The relative stability of the 1,3-thiazolidine ring was estimated to be more than 104 times higher than that of the 1,3-oxazolidine ring. © 1990.
引用
收藏
页码:6545 / 6552
页数:8
相关论文
共 40 条
[1]   NOVEL RING TRANSFORMATION OF THIAZOLIDINE TO OXAZOLIDINE - ACYL HALIDE-PROMOTED INTRAMOLECULAR REARRANGEMENT OF 4(R)-HYDROXYMETHYL-3-METHYL-1,3-THIAZOLIDINE [J].
ANDO, W ;
TAKATA, T ;
HUANG, L ;
TAMURA, Y .
TETRAHEDRON LETTERS, 1985, 26 (07) :869-872
[2]   ACYLATION OF 2,4-DISUBSTITUTED THIAZOLIDINES AND OXAZOLIDINES - CONCOMITANT EPIMERIZATION AT C-2 [J].
ANDO, W ;
IGARASHI, Y ;
HUANG, L .
CHEMISTRY LETTERS, 1987, (07) :1361-1364
[3]   SYNTHESIS OF OXAZOLIDINES, THIAZOLIDINES, AND 5,6,7,8-TETRAHYDRO-1H,3H-PYRROLO[1,2-C]OXAZOLE (OR THIAZOLE)-1,3-DIONES FROM BETA-HYDROXY-ALPHA-AMINO OR BETA-MERCAPTO-ALPHA-AMINO ACID-ESTERS [J].
BADR, MZA ;
ALY, MM ;
FAHMY, AM ;
MANSOUR, MEY .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (06) :1844-1847
[4]   INTRAMOLECULAR HYDROGEN BONDING .2. THE DETERMINATION OF HAMMETT SIGMA-CONSTANTS BY INTRAMOLECULAR HYDROGEN BONDING IN SCHIFF BASES [J].
BAKER, AW ;
SHULGIN, AT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (07) :1523-1529
[5]  
BERGMANN ED, 1959, RECL TRAV CHIM PAY B, V8, P289
[6]  
CAPITAN F, 1987, REV ROUM CHIM, V32, P151
[7]   STEREOSPECIFIC TOTAL SYNTHESIS OF D-BIOTIN FROM L(+)-CYSTEINE [J].
CONFALONE, PN ;
PIZZOLATO, G ;
BAGGIOLINI, EG ;
LOLLAR, D ;
USKOKOVIC, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (21) :7020-7026
[8]   RING-CHAIN TAUTOMERISM OF 1,3-OXAZOLIDINES PREPARED FROM NOREPHEDRINE AND NORPSEUDOEPHEDRINE [J].
FULOP, F ;
BERNATH, G ;
MATTINEN, J ;
PIHLAJA, K .
TETRAHEDRON, 1989, 45 (13) :4317-4324
[9]  
FULOP F, 1988, TETRAHEDRON, V44, P2993
[10]   RING CHAIN TAUTOMERISM IN 1,3-OXAZINES [J].
FULOP, F ;
PIHLAJA, K ;
MATTINEN, J ;
BERNATH, G .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (17) :3821-3825