Synthesis and Structure of Novel 1-Aryl-4,4,4-trichloro-1,3-butanediones

Novel 1-aryl-4,4,4-trichloro-1,3-butanediones in good yields (80-97%) were synthesized in one pot through acetal acylation with trichloroacetyl chloride followed by acid hydrolysis. Structures of all compounds were elucidated by elemental analysis, mass spectrometry, and 1 H/ 13 C nuclear magnetic r...

Full description

Saved in:

Bibliographic Details
Published in:	Synthetic communications Vol. 42; no. 5; pp. 727 - 737
Main Authors:	Flores, Alex F. C., Martins, Mauro J., Frigo, Leandro M., Machado, Pablo, Campos, Patrick T., Malavolta, Juliana L.
Format:	Journal Article
Language:	English
Published:	Philadelphia Taylor & Francis Group 01-03-2012 Taylor & Francis Ltd
Subjects:	Acetal acylation diketones keto-enol equilibrium trichloromethyl
Online Access:	Get full text
Tags:	Add Tag No Tags, Be the first to tag this record!

Description
Summary:	Novel 1-aryl-4,4,4-trichloro-1,3-butanediones in good yields (80-97%) were synthesized in one pot through acetal acylation with trichloroacetyl chloride followed by acid hydrolysis. Structures of all compounds were elucidated by elemental analysis, mass spectrometry, and 1 H/ 13 C nuclear magnetic resonance (NMR) measurements. The 1 H/ 13 C NMR data showed that trichloromethyl- β -diketones 2a-k in solution are predominantly ketoenol. However, the spectroscopic data from 4,4,4-trichloro-2-methyl-1-phenyl-1,3-butabedione (2l) with methyl substituent between carbonyls showed a bias toward the diketo form in solution. X-ray diffraction of monocrystals from 2g and 2i showed that these compounds are cis-ketoenol tautomers. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communcations® to view the free supplemental file.
ISSN:	0039-7911 1532-2432
DOI:	10.1080/00397911.2010.530376