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Stereochemistry and some synthetic uses of the heteroarylation of phospholes

✍ Scribed by Eliane Deschamps; Louis Ricard; François Mathey


Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
534 KB
Volume
2
Category
Article
ISSN
1042-7163

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✦ Synopsis


Further studies have been conducted on the condensation ofelectron-rich arenes or heteroarenes with the dienic system of phosphole P-complexes. According to the X-ray crystal structure analysis of one o f the resulting 2-aryl-3-phospholene P-complexes, the condensation takes place on the side of the diene opposite to the complexing group. The decomplexation o f the phospholene P-Mo(CO)~ and P-W(CO)5 complexes, respectively, bv reaction with sulfur or halogens and tertiary amines yields the corresponding P-sulfides and oxides with full retention of the stereochemistry at phosphorus. Double condensation of the phosphole P-complexes onto the 2 and 5 positions of thiophene and furan ultimately leads to phospholethiophene-phosphole and phosphole-furanphosphole chuins. The first type has been characterized by X-ray crystal structure analysis of its P,P-disulfide. N o electronic delocalization appears to take place along the chain.

Dedicated to Marianne Baudler on the occasion of her sev-"To whom correspondence should be addressed.

entieth birthday this paper, we wish to establish the stereochemistry of the arylation and decomplexation steps and to show how it is possible to use this methodology to build original tricyclic systems that could be used for the building of polyphosphole chains. Such chains may have some potential in the conception of new electroconducting polymers [21.


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