Fragmentation of trifluoromethylated alkenes and acetylenes by N,N-binucleophiles. Synthesis of imidazolines or imidazolidines (oxazolidines) controlled by substituent

Valentine G Nenajdenko; Vasiliy M Muzalevskiy; Aleksey V Shastin; Elizabeth S Balenkova; Evgeniy V Kondrashov; Igor A Ushakov; Alexander Yu Rulev

doi:10.1021/jo101107t

Fragmentation of trifluoromethylated alkenes and acetylenes by N,N-binucleophiles. Synthesis of imidazolines or imidazolidines (oxazolidines) controlled by substituent

J Org Chem. 2010 Aug 20;75(16):5679-88. doi: 10.1021/jo101107t.

Authors

Valentine G Nenajdenko¹, Vasiliy M Muzalevskiy, Aleksey V Shastin, Elizabeth S Balenkova, Evgeniy V Kondrashov, Igor A Ushakov, Alexander Yu Rulev

Affiliation

¹ Department of Chemistry, Moscow State University, Leninskie Gory, Moscow 119992, Russia. nen@acylium.chem.msu.ru

PMID: 20669939
DOI: 10.1021/jo101107t

Abstract

The reaction of beta-halogeno-beta-polyfluoromethylstyrenes with N,N- or N,O-binucleophiles leads to unexpected fragmentation products (imidazolines) or to heterocyclization giving CF(3)-substituted imidazolidines (N,N-) and oxazolidines (N,O-) depending on aryl substituent. The scope and the reaction mechanism are discussed.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes / chemistry*
Alkynes / chemistry*
Imidazolidines / chemical synthesis*
Imidazolidines / chemistry
Imidazolines / chemical synthesis*
Imidazolines / chemistry
Molecular Structure
Stereoisomerism

Substances

Alkenes
Alkynes
Imidazolidines
Imidazolines