ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The reaction of triethyl and trimethyl phosphites with 10-methyleneanthrone 1a, 10-benzylideneanthrone 1b, 10-(p-chlorobenzylidene)anthrone 1c, 10-(p-methoxybenzylidene)anthrone 1d and 10-(diphenylmethylene)anthrone 1e, has been investigated. Depending on the experimental conditions, reaction of 1a with triethyl phosphite gives diethyl (10-ethoxy-9-anthryl)methylphosphonate 3a and/or the spiroanthrone 8a, whereas, with trimethyl phosphite, dimethyl [(9, 10-dihydro-10-oxo-9-anthryl)methyl]phosphonate 11a is formed. Compound 1b on reaction with trimethyl phosphite yields dimethyl [α-(9,10-dihydro-10-oxo-9-anthryl) benzyl]phosphonate 11b. Reaction of 1c with triethyl phosphite and trimethyl phosphite gives rise to diethyl [p-chloro-α-(10-ethoxy-9-anthryl)benzyl]phosphonate 3c and dimethyl [p-chloro-α-(9,10-dihydro-10-oxo-9-anthryl)benzyl]phosphonate 11c respectively. Compounds 1d and 1e did not react with alkyl phosphites.Possible reaction mechanisms are considered and the structural assignments are based on analytical and spectroscopic results.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19743160305
Permalink