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Molecules 2012, 17(1), 1-14; doi:10.3390/molecules17010001

Facile Preparation of the Tosylhydrazone Derivatives of a Series of Racemic trans-3,4-Substituted Cyclopentanones

Department of Chemistry, American University of Beirut, Beirut 11-0236, Lebanon
Department of Chemistry, Lebanese University, Hadath 6573-14, Lebanon
Author to whom correspondence should be addressed.
Received: 14 November 2011 / Revised: 19 December 2011 / Accepted: 19 December 2011 / Published: 22 December 2011
(This article belongs to the Section Organic Synthesis)
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We report the synthesis and characterization of a variety of trans-3,4-substituted cyclopentanones and the corresponding tosylhydrazone derivatives starting with diethyl fumarate. Protection of the keto group followed by selective monohydrolysis of esters was achieved, resulting in cyclopentanones with different substituents at positions 3 and 4. The tosylhydrazone derivative of each cyclopentanone intermediate was prepared in moderate to good yields. These compounds are potential precursors for functionalized methanofullerenes.
Keywords: tosyl hydrazone; cyclopentanone; ethylene ketal; monohydrolysis tosyl hydrazone; cyclopentanone; ethylene ketal; monohydrolysis

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Bouhadir, K.H.; Aleiwe, B.A.; Fares, F.A. Facile Preparation of the Tosylhydrazone Derivatives of a Series of Racemic trans-3,4-Substituted Cyclopentanones. Molecules 2012, 17, 1-14.

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