TY - JOUR
T1 - Nonstabilised azomethine ylids from N-oxides
T2 - unravelling the deprotonation of N-methylmorpholine N-oxide
AU - Mirzayans, Paul Malek
AU - Krenske, Elizabeth H.
AU - Williams, Craig M.
PY - 2014/6/4
Y1 - 2014/6/4
N2 - Nonstabilised azomethine ylids (NAYs) are useful 1,3-dipoles, but their synthetic applications are restricted by the high temperatures often needed for their generation, and by an incomplete understanding of the effect of heteroatoms in cyclic systems. We have examined the behaviour of N-methylmorpholine N-oxide (NMO) as a NAY precursor in the Roussi reaction (low-temperature reaction of an N-oxide with strong base). The choice of base is critical to achieving cycloadduct formation. We report synthetic and computational (density functional theory) investigations of the products obtained with different bases and their mechanisms of formation.
AB - Nonstabilised azomethine ylids (NAYs) are useful 1,3-dipoles, but their synthetic applications are restricted by the high temperatures often needed for their generation, and by an incomplete understanding of the effect of heteroatoms in cyclic systems. We have examined the behaviour of N-methylmorpholine N-oxide (NMO) as a NAY precursor in the Roussi reaction (low-temperature reaction of an N-oxide with strong base). The choice of base is critical to achieving cycloadduct formation. We report synthetic and computational (density functional theory) investigations of the products obtained with different bases and their mechanisms of formation.
UR - http://www.scopus.com/inward/record.url?scp=84906853369&partnerID=8YFLogxK
UR - http://purl.org/au-research/grants/arc/FT110100851
UR - http://purl.org/au-research/grants/arc/FT120100632
U2 - 10.1071/CH14217
DO - 10.1071/CH14217
M3 - Article
AN - SCOPUS:84906853369
SN - 0004-9425
VL - 67
SP - 1309
EP - 1317
JO - Australian Journal of Chemistry
JF - Australian Journal of Chemistry
IS - 9
ER -