ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Tetrazole Compounds. 4. Alkylation of 1-Aryl-5-(2-dimethylamino-vinyl)-1 H-tetrazolesAlkylation of 1-aryl-5-(2-dimethylamino-vinyl)-1 H-tetrazoles 1 with dialkyl sulfates or alkyl iodides yields mainly 4-alkyl-1-aryl-5-(2-dimethylamino-vinyl)-1 H-tetrazolium salts which can be isolated free from isomers by separation as perchlorates 2. The reaction proceeds with retention of the E configuration of the vinyl group. In contrast to 1 the methyl groups of the dimethylamino substituent in 2 are magnetically non-equivalent indicating restricted rotation of this residue. On heating 2 with aqueous mineral acids the dimethylaminovinyl moiety undergoes degradation to a methyl group affording 4-alkyl-1-aryl-5-methyl-1 H-tetrazolium salts 4, the structure of which was confirmed by independent synthesis. With hot aqueous alkali hydroxide 2 reacts under ring cleavage to give aryl azide. - 1H n.m.r. and u.v. spectroscopic data of the tetrazolium salts 2 and 4 are reported.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19893310602
