ISSN:
0009-2940
Keywords:
Diels-Alder reaction
;
Vinyl allenes
;
Acetylenecarboxylates
;
Phosphonates
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
1,5-Sigmatropic Rearrangements of Diels-Alder Adducts in the Reaction of Alkatrienylphosphonates with Alkyl Acetylenecarboxylates - A New Method for the Synthesis of Benzyl- and PhenylphosphonatesThe reaction of dialkyl (3-methyl-1,2,4-pentatrienyl)- and dialky] (3-methyl-1-vinyl-1,2-butadienyl)phosphonic acids 1a-d an 5a, b, respectively, with alkyl esters of the acetylenecarboxylic acids 2a-d proceeds via 1,5-sigmatropic rearrangement and aromatization of the initially formed Diels-Alder adducts. The reaction with the unsymmetrical dienophiles 2a, b occurs with preferred formation of the cycloadducts A, leading to the benzylphosphonates 3a-h. The above reaction constitutes a new method for the preparation of difficulty accessible derivatives of the benzyl- and phenylphosphonic acids. The aromatic structures of the obtained compounds 3a-h, 4a-f, and 6a-d were proved by their IR, mass, and 1H-NMR spectra.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19901230630
