ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Nucleophilic Aminomethylation of Ketones and Organic Halides with 1,l-Diphenyl-2-azaallyllithiumN-(Diphenylmethylene)methylamine (1a) is metalated to 1,1-diphenyl-2-azaallyIlithium (1b) by lithium diisopropylamide. Ketones react with 1b and subsequently with water to give alkylidene-amino alcohols(2). These compounds give rise to β-amino alcohols 3( = aminomethylation product) on hydrolytic cleavage with acids, whereas dehydration with thionyl chloride/pyridine provides an entry to the 2-aza-1,3-butadienes 4. Organic halides ( = alkyl bromides, allyl bromide) react with 1b to yield imines 5 which on acidic hydrolysis form amines 6 (= aminomethylation product).
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19771100724
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