REACTION OF ARYL BIPHENYL-2-YL THIOKETONES WITH DITOSYLDIAZOMETHANE - INTERNAL CYCLIZATION OF THE THIOKETONE S-METHYLIDES TO AFFORD BENZO[C]THIOPHENE DERIVATIVES - STRUCTURE DETERMINATION OF THE PRODUCTS BY RANEY-NICKEL DEGRADATION AND X-RAY CRYSTALLOGRAPHIC ANALYSIS

被引：15

作者：

SAITO, T ^{[1
]}

AYUKAWA, H ^{[1
]}

SUMIZAWA, N ^{[1
]}

SHIZUTA, T ^{[1
]}

MOTOKI, S ^{[1
]}

KOBAYASHI, K ^{[1
]}

机构：

[1] INST PHYS & CHEM RES,WAKO,SAITAMA 35101,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 06期

关键词：

D O I：

10.1039/p19910001405

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of arylbiphenyl-2-yl thioketones 1 with ditosyldiazomethane in the presence of copper acetylacetonate has been investigated. It involves internal cycloaddition of intermediary thioketone S-methylides 8 and 23 to afford eventually benzo[c]thiophene derivatives 16, and 24 and 25, respectively. The structure of product 16 was determined by means of spectroscopy and chemical evidence. Furthermore the structure was unambiguously established by X-ray crystallographic analysis of compound 16c (X = MeO). The results are discussed in terms of cyclisation/rearrangement of the transient thioketone S-methylides 8 and 23 as a key step in consideration of the other plausible routes leading to their structural isomers 10, 11, 14, 15 and 17.

引用

页码：1405 / 1410

页数：6

共 42 条

[1] STRUCTURE OF THIOPHENE [J].