1,1-BIS(METHYLTHIO)-2-NITROETHENE IN SUPERACIDS - NMR-STUDY AND REACTIVITY OF THE FORMED HYDROXYNITRILIUM ION

Authors
COUSTARD JM
Citation
Jm. Coustard, 1,1-BIS(METHYLTHIO)-2-NITROETHENE IN SUPERACIDS - NMR-STUDY AND REACTIVITY OF THE FORMED HYDROXYNITRILIUM ION, Tetrahedron, 51(40), 1995, pp. 10929-10940
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
40
Year of publication
1995
Pages
10929 - 10940
Database
ISI
SICI code
0040-4020(1995)51:40<10929:1IS-NA>2.0.ZU;2-A
Abstract
At low temperature in superacids TFSA or HF-SbF5, 1,1-bis(methylthio)- 2-nitroethene yields a stable dication with hydroxynitrilium and bis(m ethylthio)carbocationic sites. The first site can be trapped in situ w ith suitable nucleophiles (aromatics, fluoride). Both sites can be tra pped when the acidity is destroyed with MeOH or MeSH, to form in fan t o good yield the corresponding alpha-hydroxyiminoorthothioester or the furoxane orthothioester.