Facile synthesis and rearrangement of propargylic trifluoromethanesulfinates

Authors
Braverman, S Pechenick, T Zafrani, Y
Citation
S. Braverman et al., Facile synthesis and rearrangement of propargylic trifluoromethanesulfinates, TETRAHEDR L, 42(7), 2001, pp. 1391-1393
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
7
Year of publication
2001
Pages
1391 - 1393
Database
ISI
SICI code
0040-4039(20010212)42:7<1391:FSAROP>2.0.ZU;2-J
Abstract
The synthesis and reactivity of propargylic trifluoromethanesulfinates unde r various conditions have been investigated. These esters readily undergo [ 2,3]-sigmatropic rearrangement to the corresponding allenyl trifluoromethyl sulfones, even under solvolytic conditions. An unusually facile nucleophil ic addition of the solvent to the allenyl sulfone under the latter conditio ns has also been observed. (C) 2001 Elsevier Science Ltd. All rights reserv ed.