Unexpected formation of derivatives of cyclobutene and thiacyclobutane from the reaction between dilithiated benzylacetylene and isothiocyanates

✍ Scribed by Lambert Brandsma; Anthony L Spek; Boris A Trofimov; Ol'ga A Tarasova; Nina A Nedolya; Andrei V Afonin; Sergei V Zinshenko

• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 51 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)00787-0

✦ Synopsis

Reaction of dilithiated benzylacetylene PhCH(Li)-C C-Li with one equivalent of an isothiocyanate RN C S followed by successive addition of t-BuOH, a solution of t-BuOK in DMSO and methyl iodide gives exclusively a cyclobutene or a thietane derivative if R=t-Bu or Ph, respectively, and mixtures of the expected thiophene, the cyclobutene and thietane derivatives if R=Me.