ISSN:
0941-1216
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Photochemistry of Aminoketones. XV. Photochemical Acyl Migration in N-Tosyl-β-aminovinyl-phenyl-ketonesN-Tosyl-β-aminovinyl-phenyl-ketones 1a - i are prepared in good yields from β-chlorovinyl- phenyl-ketones by reaction with the sodium salts of tosyl amides in dry DMF at room temperature. In contrast to the relatively photostable N, N-dialkyl-β-aminovinyl-aryl-ketones the electronically excited 1 give irreversible chemical reactions within a few minutes. Among other not identified photoproducts the α-tosyl-β-aminovinyl-phenyl-ketones 2 were found. From the experimental results it is evident that the migration of the tosyl group prefers a radical-type two step reaction through an intermediate X/Y of a (1,5)-N→O-tosylrearrangement.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19933350107
