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Sulfur-Nitrogen Heterocycles
Molecules 2005, 10(2), 321-326; doi:10.3390/10020321
Article

1,3-Dipolar Cycloaddition Reactions of 1-(4-Phenylphenacyl)-1,10-phenanthrolinium N-Ylide with Activated Alkynes and Alkenes

1,* , 2, 1, 1 and 1
1 Centre of Organic Chemistry "C. D. Nenitzescu", Romanian Academy, Spl. Independentei 202B, Bucharest 060023, Romania 2 Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa
* Author to whom correspondence should be addressed.
Received: 8 October 2004 / Revised: 4 November 2004 / Accepted: 10 November 2004 / Published: 28 February 2005
(This article belongs to the Special Issue Sulfur-Nitrogen Heterocycles)
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Abstract

The 3 2 cycloaddition reaction of 1-(4-phenylphenacyl)-1,10-phenanthrolinium ylide with activated alkynes gave pyrrolo[1,2- 4a][1,10]phenanthrolines 6a-d. The "one pot" synthesis of 6a,b,d from 4, activatedalkenes, Et3N and tetrakis-pyridine cobalt (II) dichromate (TPCD) is described. Thehelical chirality of pyrrolophenanthrolines 6b-d was put in evidence by NMRspectroscopy.
Keywords: N-ylides; 1; 3-dipolar cycloaddition; pyrrolophenanthrolines; helical chirality. N-ylides; 1; 3-dipolar cycloaddition; pyrrolophenanthrolines; helical chirality.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Dumitrascu, F.; Caira, M.R.; Draghici, C.; Caproiu, M.T.; Badoiu, A. 1,3-Dipolar Cycloaddition Reactions of 1-(4-Phenylphenacyl)-1,10-phenanthrolinium N-Ylide with Activated Alkynes and Alkenes. Molecules 2005, 10, 321-326.

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