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

Authors
Brandsma, L Spek, AL Trofimov, BA Tarasova, OA Nedolya, NA Afonin, AV Zinshenko, SV
Citation
L. Brandsma et al., Unexpected formation of derivatives of cyclobutene and thiacyclobutane from the reaction between dilithiated benzylacetylene and isothiocyanates, TETRAHEDR L, 42(28), 2001, pp. 4687-4689
Citations number
9
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
28
Year of publication
2001
Pages
4687 - 4689
Database
ISI
SICI code
0040-4039(20010709)42:28<4687:UFODOC>2.0.ZU;2-M
Abstract
Reaction of dilithiated benzylacetylene PhCH(Li)-C=C-Li with one equivalent of an isothiocyanate RN-C=S followed by successive addition of r-BuOH, a s olution 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 th e expected thiophene. the cyclobutene and thietane derivatives if R = Me, ( C) 2001 Published by Elsevier Science Ltd.