Tris[(5-chloro-2-thienyl)methyl] phosphine oxide from elemental phosphorusand 2-chloro-5-(chloromethyl) thiophene

Authors
Gusarova, NK Arbuzova, SN Shaikhudinova, SI Kazantseva, TI Reutskaya, AM Ivanova, NI Papernaya, L Trofimov, BA
Citation
Nk. Gusarova et al., Tris[(5-chloro-2-thienyl)methyl] phosphine oxide from elemental phosphorusand 2-chloro-5-(chloromethyl) thiophene, PHOSPHOR SU, 175, 2001, pp. 163-167
Citations number
6
Categorie Soggetti
Inorganic & Nuclear Chemistry
Journal title
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
ISSN journal
10426507 → ACNP
Volume
175
Year of publication
2001
Pages
163 - 167
Database
ISI
SICI code
1042-6507(2001)175:<163:TPOFEP>2.0.ZU;2-4
Abstract
White phosphorus readily reacts with 2-chloro-5-(chloromethyl)thiophene und er phase-transfer conditions (KOH, water, dioxane, benzyltriethylammonium c hloride, 50-52 degreesC, 3 h) to form tris[(5-chloro-2-thienyl)methyl]phosp hine oxide in good yield. This new phosphine oxide undergoes the Wittig - H orner reaction with benzaldehyde (NaNH2/THF system) leading to 2-chloro-5-[ (E)-2-phenylethenyl]thiophene and bis[(5-chloro-2-thienyl)methyl]phosphinic acid.