Syntheses of 4-acyl-1-methylthiabenzene 1-oxides and their 2-aza analogs

✍ Scribed by Y. Tamura; T. Miyamoto; H. Taniguchi; K. Sumoto; M. Ikeda

• Book ID: 104246971
• Publisher: Elsevier Science
• Year: 1973
• Tongue: French
• Weight: 172 KB
• Volume: 14
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)96039-3

✦ Synopsis

The chemistry of thiabenzene l-oxide and its aza analogs is of substantial intrinsic interest as one of heterocycles containing six n-electrons in the ring Recently several synthetic methods for these compounds have been achieved.

l-5

One of the most commonly used methods involves the reaction of acylacetylenes and dimethyl sulfoxonium methylids (I)1'2 or dimethyl sulfoximine (II).3 We now wish to report a general method for 4-acyl-1-methylthiabenzene l-oxides and their 2-aza analogs,which are new classes of derivatives of thiabenzene l-oxides and not accessible by the known procedures. This method involves the use of 2,2-diacyl-1-alkoxyethylenes in place of acylacetylenes.

In some cases, the intermediate 2,2-diacylvinyl-stabilized ylides or imines could be isolated.

lo. 20 stable.

For example, it aid not react with benzoyl chloride or acetyl chloride under refluxing conditions to recover unchanged.