๐”– Bobbio Scriptorium
โœฆ   LIBER   โœฆ

Alkylation of aldehyde oxime dianions

โœ Scribed by Robert E. Gawley; Tibor Nagy

Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
88 KB
Volume
25
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

โœฆ Synopsis

In contrast to an earlier report, aldoximes can be deprotonated to their dianions and alkylated in high yield.

In 1976, Kofronl and JungL reported that ketone oximes could be deprotonated and alkylated regiospecifically syn to the oxime hydroxyl. In his report, Kofron noted that "attempts to alkylate acetaldehyde oxime gave no identifiable product." He further stated that propionaldehyde oxime could be alkylated in low yield, and that major byproducts appeared to be nitriles.

1 Because of our interest in studying aldoximes as substrates in the oxime rearrangement cyclization, 3 we undertook a reinvestigation of aldoxime alkylation.

๐Ÿ“œ SIMILAR VOLUMES

Reactions of oxime dianions: Stereospeci
Reactions of oxime dianions: Stereospecificity in alkylation
โœ Michael E. Jung; Patricia A. Blair; John A. Lowe ๐Ÿ“‚ Article ๐Ÿ“… 1976 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 223 KB

Several years ago Hauser observed that treatment of aromatic ketoximes with two equivalents of strong base resulted in the formation of dianions which could be successfully alkylated on n carbon.L However, no information on the stereochemistry of the alkylated products was ever reported. We now wish

Alkylation of the chrysin dianion
Alkylation of the chrysin dianion
โœ J.J. Beirne; N.M. Carroll; W.I. O'Sullivan; J. Woods ๐Ÿ“‚ Article ๐Ÿ“… 1975 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 279 KB
The formation and alkylation of ฮฑ-ketoam
The formation and alkylation of ฮฑ-ketoamide dianions
โœ Emil R Koft; Michael D Williams ๐Ÿ“‚ Article ๐Ÿ“… 1986 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 171 KB

Alpha ketoamides may be deprotonated twice with stronq base. The dianions so formed react with alkyl halides to yield cl-amid0 tertiary alcohols. The extended enolates of crotonic acid derivatives 'anb have become valuable reactive intermediates in the preparation of R,y-unsaturated carbonyl compou