Font Size: a A A

Amine Conversion And Synthesis Of. The Barbier-type Reaction System And Phi (oac) <sub> 2 </ Sub> Reaction System

Posted on:2010-01-02Degree:MasterType:Thesis
Country:ChinaCandidate:D M PuFull Text:PDF
GTID:2191360275491669Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
This thesis focuses on the transformation of amines and imines under the condition of Barbier-type reactions,and also the synthesis of aziridines catalyzed by the PhI(OAc)2/I2 system.In the first part,we studied the nucleophilic addition reactions of aldehyde, amine,Zinc and benzyl bromide in one pot to afford homobenzyl and homoallyl amines in moderate to good yields.Based on the experimental results,a six-member-ring intermediate was proposed as the mechanism for these reactions. Moreover,we found that it can also afford good yields to different aldehydes and amines by using this method.In the second part,we alternated amines to sulfonamides under the same reaction system and found that N-sulfonyl aldimine was formed.Meanwhile,we discovered that kinds of aldehydes,such as phenyl and acyclic aldehydes,and N-sulfinyl can also give similar results in mild conditions.A four-member-ring intermediate was proposed as the mechanism for these reactions.In the last part we studied the application of PhI(OAc)2/I2 in the synthesis of aziridines.The yield was promoted to be good after the optimization of reaction conditions.
Keywords/Search Tags:Barbier-type reaction, imine, periodate, aziridine
PDF Full Text Request
Related items