One-pot preparation of 2,7-disubstituted cycloheptanones and their ring-closing metatheses
Presentation Type
Poster
Department
Chemistry
Abstract
2,7-Disubstituted cycloheptanones 2 were prepared via a one-pot procedure from the imine (R = cyclohexyl) and hydrazone (R = NMe2) of cycloheptanone that involves sequential deprotonation, alkylation, deprotonation, alkylation and hydrolysis. Many of the dialkylation products underwent successful ring-closing metathesis (RCM) under infinite dilution conditions. We have also examined the dialkylation of the N,N-dimethylhydrazones of cyclopentanone and cyclohexanone, and determined the equilibrium trans/cis ratios of 2,5-disubstituted cyclopentanones, 2,6-disubstituted cyclohexanones and 2,7-disubstituted cycloheptanones.
Faculty Mentor
Dr. James White
Location
Waves Cafeteria
Start Date
23-3-2018 2:00 PM
End Date
23-3-2018 3:30 PM
One-pot preparation of 2,7-disubstituted cycloheptanones and their ring-closing metatheses
Waves Cafeteria
2,7-Disubstituted cycloheptanones 2 were prepared via a one-pot procedure from the imine (R = cyclohexyl) and hydrazone (R = NMe2) of cycloheptanone that involves sequential deprotonation, alkylation, deprotonation, alkylation and hydrolysis. Many of the dialkylation products underwent successful ring-closing metathesis (RCM) under infinite dilution conditions. We have also examined the dialkylation of the N,N-dimethylhydrazones of cyclopentanone and cyclohexanone, and determined the equilibrium trans/cis ratios of 2,5-disubstituted cyclopentanones, 2,6-disubstituted cyclohexanones and 2,7-disubstituted cycloheptanones.