2,3-Dihydronaphtho[1,2-b]thiophene 1-oxides in the synthesis of 2,3-dihydronaphtho- and naphtho[1,2-b]thiophenes

✍ Scribed by N. V. Fedorov; A. V. Anisimov; E. A. Viktorova

• Publisher: Springer US
• Year: 1989
• Tongue: English
• Weight: 337 KB
• Volume: 25
• Category: Article
• ISSN: 0009-3122
• DOI: 10.1007/bf00473863

✦ Synopsis

2,3-Dihydronaphtho[l,2-b]thiophene 1-oxides, obtained by thermolysis of alkyl lnaphthyl sulfoxides, are reduced by lithium aluminum hydride to 2,3-dihydronaphtho[l,2-b]thiophenes, whereas under the influence of acetic and trifluoroacetic anhydrides they form naphtho[l,2-b]thiophenes. Compounds of the dihydronaphtho-and naphthothiophene series are of interest as subjects that model individual components of the higher fractions of high-sulfur petroleum oils [i] and potential starting substances for the synthesis of compounds that have the properties of pesticides, light sensitizers, etc. In the present research to obtain 2,3-dihydronaphthoand naphtho[l,2-b]thiophenes we used transformations of 2,3-dihydronaphtho[l,2-b]thiophene 1-oxides Ilia, b, which are formed as a result of 3,3-sigmatropic rearrangement of the corresponding allyl l-naphthyl sulfoxidesla, b, through the intermediate sulfenic acids !la, b with their subsequent cyclization [2, 3]: x a,b iIa~b l-III a R=H;b R=CH~ O,~S ,, CH~ IIIa,b