Next Article in Journal
Nematocidal Flavone-C-Glycosides against the Root-Knot Nematode (Meloidogyne incognita) from Arisaema erubescens Tubers
Next Article in Special Issue
Computational and Spectral Investigation of 5,12-Dihydro-5,12-ethanonaphthacene-13-carbaldehyde
Previous Article in Journal
Cholesterol-Lowering Activity of the Major Polyphenols in Grape Seed
Previous Article in Special Issue
Selenol Protecting Groups in Organic Chemistry: Special Emphasis on Selenocysteine Se-Protection in Solid Phase Peptide Synthesis
Open AccessArticle

Two-Carbon Homologation of Aldehydes and Ketones to α,β-Unsaturated Aldehydes

1
Unit of Crop Bioprotection Research, USDA, Agricultural Research Service, National Center for Agricultural Utilization Research, 1815 N. University Street, Peoria, IL 61604, USA
2
Unit of Functional Food Research, USDA, Agricultural Research Service, National Center for Agricultural Utilization Research, 1815 N. University Street, Peoria, IL 61604, USA
*
Author to whom correspondence should be addressed.
Molecules 2011, 16(6), 5062-5078; https://doi.org/10.3390/molecules16065062
Received: 28 April 2011 / Revised: 31 May 2011 / Accepted: 13 June 2011 / Published: 17 June 2011
(This article belongs to the Special Issue Protecting Group in Organic Synthesis)
Phosphonate reagents were developed for the two-carbon homologation of aldehydes or ketones to unbranched- or methyl-branched α,β-unsaturated aldehydes. The phosphonate reagents, diethyl methylformyl-2-phosphonate dimethylhydrazone and diethyl ethylformyl-2-phosphonate dimethylhydrazone, contained a protected aldehyde group instead of the usual ester group. A homologation cycle entailed condensation of the reagent with the starting aldehyde, followed by removal of the dimethylhydrazone protective group with a biphasic mixture of 1 M HCl and petroleum ether. This robust two-step process worked with a variety of aldehydes and ketones. Overall isolated yields of unsaturated aldehyde products ranged from 71% to 86% after the condensation and deprotection steps. View Full-Text
Keywords: aldehyde homologation; ketone to aldehyde homologation; diethyl methylformyl-phosphonate dimethylhydrazone; diethyl ethylformyl-2-phosphonate dimethylhydrazone aldehyde homologation; ketone to aldehyde homologation; diethyl methylformyl-phosphonate dimethylhydrazone; diethyl ethylformyl-2-phosphonate dimethylhydrazone
Show Figures

Scheme 1

MDPI and ACS Style

Petroski, R.J.; Vermillion, K.; Cossé, A.A. Two-Carbon Homologation of Aldehydes and Ketones to α,β-Unsaturated Aldehydes. Molecules 2011, 16, 5062-5078. https://doi.org/10.3390/molecules16065062

AMA Style

Petroski RJ, Vermillion K, Cossé AA. Two-Carbon Homologation of Aldehydes and Ketones to α,β-Unsaturated Aldehydes. Molecules. 2011; 16(6):5062-5078. https://doi.org/10.3390/molecules16065062

Chicago/Turabian Style

Petroski, Richard J.; Vermillion, Karl; Cossé, Allard A. 2011. "Two-Carbon Homologation of Aldehydes and Ketones to α,β-Unsaturated Aldehydes" Molecules 16, no. 6: 5062-5078. https://doi.org/10.3390/molecules16065062

Find Other Styles

Article Access Map by Country/Region

1
Only visits after 24 November 2015 are recorded.
Search more from Scilit
 
Search
Back to TopTop