Double allylation reactions of (2-azaallyl)stannanes: synthesis of N,N-bis(3-butenyl)amines and their conversion to 2,3,6,7-tetrahydroazepines via ring-closing metathesis.
[reaction in text] Treatment of (2-azaallyl)stannanes (i) with 2.2 equiv of allylmagnesium bromide afforded good yields of N,N-bis(3-butenyl)amines derivatives (ii), which were subjected to ring-closing metathesis to afford 2,3,6,7-tetrahydroazepines (iii). Thus, (2-azaallyl)stannanes are the synthetic equivalents of amine alpha,alpha'-dications.
Pearson
W H
WH
Department of Chemistry, The University of Michigan, Ann Arbor, Michigan 48109-1055, USA. wpearson@umich.edu
Aponick
A
A
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry*; D001381:Azepines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D017971:Tin Compounds / Q000737:chemistry*
D000475:Alkenes; D000588:Amines; D001381:Azepines; D017971:Tin Compounds