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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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