STEREOCHEMISTRY AND STRUCTURE IN TETRAHYDRO-1-THIO-4-PYRONE AND TETRAHYDRO-4-PYRONE SERIES

被引:48
作者
BAXTER, CAR
WHITING, DA
机构
[1] Department of Chemistry, University College (University of Wales), Cardiff
来源
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC | 1968年 / 09期
关键词
D O I
10.1039/j39680001174
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The preparation of the geometric isomers of 2,6-diphenyltetrahydro-1-thio- 4-pyrone, and of its O-heterooyclic analogue is described, and configuration and conformation are assigned to each on the basis of n.m.r. spectra. In the formation of the thiopyrones from dibenzylidene acetone, the less stable isomer is shown to be kinetically favoured; a rationalisation is proposed. Evidence for a preferred quasi-boat conformation for the 5,6-dihydro-2H-thiopyran ring is presented. The structure and stereochemistry of some substituted tetrahydro-4-pyrones formed in the diethyl ketone-benzaldehyde condensation are described.
引用
收藏
页码:1174 / &
相关论文
共 9 条
[1]   1-thiopyrone and 1-thiopyranone ; Articles on the pyron problem. [J].
Arndt, F ;
Nachtwey, P ;
Pusch, J .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1925, 58 :1633-1644
[2]   Configuration-regulation of 2.6-diphenyl-phenthianone. [J].
Arndt, F ;
Schauder, E .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1930, 63 :313-316
[3]   ASPECTS OF CHEMISTRY OF HEXAHYDROISOCHROMANONE FROM CARVENONE-BENZALDEHYDE CONDENSATION [J].
BAXTER, CAR ;
FORWARD, GC ;
WHITING, DA .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (09) :1169-&
[4]   STRUCTURE AND STEREOCHEMISTRY OF HEXAHYDROISOCHROMANONE FROM CARVENONE-BENZALDEHYDE CONDENSATION [J].
BAXTER, CAR ;
FORWARD, CG ;
WHITING, DA .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (09) :1162-&
[5]  
CORNUBERT R, 1934, B SOC CHIM FR, P90
[6]  
HEILBRON, 1965, DICTIONARY ORGANIC C
[7]  
JAPP FR, 1904, J CHEM SOC, P1473
[8]  
VORLANDER D, 1896, BER DTSCH CHEM GES, V29, P1352
[9]  
WILBERG KB, 1962, INTERPRETATION NMR S