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

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

1 Department of Chemistry, American University of Beirut, Beirut 11-0236, Lebanon 2 Department of Chemistry, Lebanese University, Hadath 6573-14, Lebanon
* Author to whom correspondence should be addressed.
Received: 14 November 2011; in revised form: 19 December 2011 / Accepted: 19 December 2011 / Published: 22 December 2011
(This article belongs to the Section Organic Synthesis)
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Abstract: 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

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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.

AMA Style

Bouhadir KH, Aleiwe BA, Fares FA. Facile Preparation of the Tosylhydrazone Derivatives of a Series of Racemic trans-3,4-Substituted Cyclopentanones. Molecules. 2012; 17(1):1-14.

Chicago/Turabian Style

Bouhadir, Kamal H.; Aleiwe, Bilal Abou; Fares, Fares A. 2012. "Facile Preparation of the Tosylhydrazone Derivatives of a Series of Racemic trans-3,4-Substituted Cyclopentanones." Molecules 17, no. 1: 1-14.

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