Reactions of P(MeNCH2CH2)3N with primary, secondary, and tertiary alkyl halides: Evidence for a solvent-enhanced dehydrohalogenation

✍ Scribed by T. Mohan; S. Arumugam; T. Wang; R. A. Jacobson; J. G. Verkade

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 571 KB
• Volume: 7
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/(sici)1098-1071(199611)7:6<455::aid-hc8>3.0.co;2-7

✦ Synopsis

The reactions of P(1MeNCH,CH2),N, 1, with Mel, Etl, EtBv, n-PrBv, n-Btil, i-PrBr, PhCH,CHBrCH,, Me-CHBr(CH,),Me, s-BuBr, and t-BuBr were studied. The reactions of the primary alkyl halides produced the corresponding phosphonium cationic compounds, whereas the secondary and tertiary halides underwent elimination to form the corresponding olefins and the protonated form of 1. Based on 'H and I3C NMR studies, it appears that elimination is exclusively trans, favoring the Saytzeff jgroduct. It was also observed that this reaction is enhanced by the solvent CH,CN. The X-ray crystal structure of [Me(l)] I is also reported, featuring a transannular distance of 2.773 A (2) facilitated by a rather wide average equatorial MeN-P-NMe bond angle of 113.1' (2)".