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Réactions d'addition-élimination à partir d'hétérocycles germaniés du type R2Ge. II. Les germa-2-diazolidines-1,3

✍ Scribed by Hélène Lavayssière; Gabriel Dousse; Jacques Satgé


Publisher
John Wiley and Sons
Year
1976
Tongue
German
Weight
496 KB
Volume
59
Category
Article
ISSN
0018-019X

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✦ Synopsis


Addition-elimination reactions from germanium heterocycles 1,3-diazolidines (X = Y = NMe). -Summary. The reactivity of X-Gerrna-l,3-diazolidines with unsaturated compounds such as heterocurnulenes (CSz, PhNCO, PhNCS) and with carbonyl compounds (aldehydes and ketones) has been investigated. Generally the formation of mono-and diinsertion derivatives is observed. The elimination reactions of (EtzGeO)n and (Et&eS)a from these addition derivatives lead to corresponding carbon diazolidines.

The mechanism of these addition-elimination reactions is precised. The interest of these reactions in organic synthesis is underlined.


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Reaction of 2-methyl-2-benzyl-l,2,3,4-tetrahydroisoquinolinium iodide with sodium amide in liquid ammonia yields 76% l-orthotolyl-2-methy1-1,2,3,4-tetrahydroisoquinoline resulting from a Sommelet-Hauser rearrangement. In the same conditions, 2,2-dimethyl-1,2,3,4-tetrahydroisoquinolinium iodide yield