Probing the hydrolytic reactivity of 2-difluoromethyl pyrroles.

Autor:	Melanson JA; Department of Chemistry, Dalhousie University, P.O. Box 15000, Halifax, NS B3H 4R2, Canada. Alison.Thompson@dal.ca., Figliola C; Department of Chemistry, Dalhousie University, P.O. Box 15000, Halifax, NS B3H 4R2, Canada. Alison.Thompson@dal.ca., Smithen DA; Department of Chemistry, Dalhousie University, P.O. Box 15000, Halifax, NS B3H 4R2, Canada. Alison.Thompson@dal.ca., Kajetanowicz AK; Department of Chemistry, Dalhousie University, P.O. Box 15000, Halifax, NS B3H 4R2, Canada. Alison.Thompson@dal.ca., Thompson A; Department of Chemistry, Dalhousie University, P.O. Box 15000, Halifax, NS B3H 4R2, Canada. Alison.Thompson@dal.ca.
Jazyk:	angličtina
Zdroj:	Organic & biomolecular chemistry [Org Biomol Chem] 2016 Dec 20; Vol. 15 (1), pp. 144-152.
DOI:	10.1039/c6ob01441k
Abstrakt:	α-Difluoromethyl pyrroles were found to be stable while N-protected with an electron-withdrawing group. Due to the propensity of pyrroles to access azafulvenium-like intermediates, the C-F bonds of an α-difluoromethyl substituent are labile under hydrolytic conditions. The presence of certain electron-withdrawing substituents about the pyrrolic ring can accelerate this process, as determined through a kinetic comparison of the deprotection and subsequent hydrolysis reactions of N-protected β-aryl α-difluoromethyl pyrroles.
Databáze:	MEDLINE
Externí odkaz:	Zobrazit plný text záznamu