Fragmentation reaction of aziridinium ylids

✍ Scribed by Yoshiteru Hata; Masamichi Watanabe

• Book ID: 104245253
• Publisher: Elsevier Science
• Year: 1972
• Tongue: French
• Weight: 167 KB
• Volume: 13
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)94172-3

✦ Synopsis

Despite the very extensive study currently beiw devoted to the development of arirldine chemistry, little information is available on aziridine ylid derivatives (1). In view of this, aziridinium ylids may be of particular interest, and to investigate the properties of aziridinium ylids, we have studied the reactions of dichlorocarbene with aziridine derivatives and wish to report here a stereospecific fmgmentation reaction observed. N-Phenethylaziridinei prepared by the reaction of ethylenimine and styrene (2) was dissolved in n-pentane or ether and an excess of potassium t-butoxide was suspended in the solution at 0'. No reaction occurred at this stage, but on the addition of chloroform the reaction immediately took place.