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Use of α-Bromo Oxime Ethers in the Synthesis of 1,2-Diamines

✍ Scribed by Shatzmiller, Shimon ;Bercovici, Sorin

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
563 KB
Volume
1992
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Oxime ethers 1 react with ammonia and primary amines to give α‐amino oxime ethers. The reaction of α‐bromo oxime ethers with sodium azide affords α‐azido oxime ethers. Hydrogenolysis of the azido compounds using 5% palladium on calcium carbonate as catalyst yields the α‐amino oxime ethers. The reaction of α‐azido oxime ethers with lithium aluminum hydride gives 1,2‐ethanediamine derivatives. The reaction of azido oxime ether 13 with LiAlH~4~, and subsequently the reaction of the resulting mixture of the diamines 14 and 15 with phosgene, preferably gives cis‐4‐pentyl‐5‐methyl‐2‐imidazolidone (16) indicating that the reduction of 13 proceeds in a stereoselective manner to furnish mainly the syn‐1,2‐ethanediamine 15.

📜 SIMILAR VOLUMES

Synthesis and Use of α-Diazo Oxime Ether
Synthesis and Use of α-Diazo Oxime Ethers in the Synthesis of Ethylene Diketone Bis(O-methyloxime) Derivatives
✍ Shatzmiller, Shimon ;Bercovici, Sorin 📂 Article 📅 1992 🏛 John Wiley and Sons 🌐 English ⚖ 222 KB

## Abstract Reaction of the lithium salts of oxime ethers 4a–c with methanesulfonyl azide gives the α‐diazo oxime ethers 5a–c. These novel compounds are stable up to 90^°^C, however, they decompose thermally in refluxing CCl~4~ and with PdCl~2~ catalysis to yield the ethylene diketone bis(__O__‐met