ISSN:
0075-4617
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Metal Addition to Arylidene-and Alkylidenemetal Amides and Consecutive ReactionsThe reactions of azomethines (1) with metals have been investigated. N-(Benzylidene)diethylaluminium amide (1c) undergoes reductive dimerisation (route A) to give 2c. The intermediate in this reaction can be isolated as 6 in benzene. In polar solvents, however, the heterocycles 2,4,5-triphenylimidazole (8) and 2,3,5,6-tetraphenylpyrazine (9) are formed via consecutive reactions. Addition of potassium to N-(diphenylmethylene)diethylaluminium amide (1e) occurs according to pathway B.- In the case of N-(ethylidene)diisobutylaluminium amide (1h) metalation takes place at the azaallyl position. The influences of the N-substituents R = C6H5, (CH3)3C, (CH3)3Si and (C2H5)2Al in 1 are compared.
Notes:
Das Verhalten der Azomethine 1 gegenüber Metallen wird untersucht. Bei N-(Benzyliden)-diethylaluminiumamid (1c) tritt reduktive Dimerisierung (gemäß Weg A) zu 2c ein, das in Benzol zu 6 abgefangen wird. In polaren Lösungsmitteln entstehen dagegen über Folgereaktionen unter anderem die Heterocyclen 2,4,5-Triphenylimidazol (8) und 2,3,5,6-Tetraphenylpyrazin (9). N-(Diphenylmethylen)diethylaluminiumamid (1e) reagiert mit Kalium unter Metalladdition nach Weg B.- Bei N-(Ethyliden)diisobutylaluminiumamid (1h) findet Metallierung in Azaallylposition statt. Der Einfluß der Substituenten R = C6H5, (CH3)3C, (CH3)3Si und (C2H5)2Al am Stickstoff von 1 wird verglichen.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.197719770913
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