ISSN:
0009-2940
Keywords:
Diazirines
;
Phosphaalkynes
;
Carbenes
;
Phosphirenes
;
[2 + 1] Cycloaddition
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Organophosphorus Compounds, 48. - 1-Halogen-1H-phosphirenes from Phosphaalkynes and ChlorocarbenesHalogen-substituted carbenes (7a - i), generated by thermolysis of diazirines (11a-i), add onto phosphaalkynes (8a-c) to form the title compounds (10a-1). Initially formed 2H-phosphirenes (9) could not be detected as their subsequent conversion to the 1H-isomers 10 by a 1,3-halogen shift is very fast. Hydrolysis of 10c,e,g-i and k yields vinylphosphonous acids (17a - e). 1-Chloro-1H-phosphirenes are transformed by nucleophilic substitution into fluoro (10a,c,e → 19a-c), bromo (10c,e → 20a,b), and iodo analogs (10c,e → 21a,b) with the help of silver tetrafluoroborate, trimethylsilyl bromide, and trimethylsilyl iodide, respectively. A crystal structure analysis of 10c is reported.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19911240538
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