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Synthesis and structural characterization of isomeric coumarino-1,2-oxaphosphole derivatives

✍ Scribed by Petar J. Petrov; Alexi A. Alexiev; Galin Petrov; Gianluca Giorgi

Publisher
Journal of Heterocyclic Chemistry
Year
2005
Tongue
English
Weight
105 KB
Volume
42
Category
Article
ISSN
0022-152X

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✦ Synopsis

The coumarino-[3,4-c]-3H-10-methyl-2-oxo-2-phenyl-1,2-oxaphosphole was prepared by the addition of PhPCl 2 to 3-acetylcoumarin in the presence of acetic anhydride. Its conversion to the isomeric coumarino-[3,4-c]-9H-9-methyl-2-oxo-2-phenyl-1,2-oxaphosphole was studied in different reaction conditions. The structures of the two isomers were determined by X-ray crystallography and by ab initio molecular orbital calculations.

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The titanocene vinylidene intermediate [Cp\* 2 Ti=C=CH 2 ] (9) The azatitanacyclobutane [Cp\* 2 Ti{ΟͺNPhΟͺC(Ph)(H)Οͺ(C= CH 2 )Οͺ}] (22) was formed from the reaction between 9 and reacted with the carbodiimides RΟͺN=C=NΟͺR [R = p-CH 3 C 6 H 4 (19a), C 6 H 11 (19b)] to give the N=C-cycloaddition benzylidene