Abstract
A new methodology for 2-aza-1,3-diene synthesis involving protodesilylation reactions of N-1-triethylsilylallyl-imines and their propargyl analogs is described. Synthetic sequences for the preparation of these allyl and propargyl imines starting with propargyl amine are presented. The silylallyl and silylpropargyl imines are transformed to 2-azadiene products by use of CsF induced desilylation via a pathway involving generation and regioselective γ-protonation of intermediate 1-imino-allyl and propargyl anions. Alkylative-desilylation of the silylallyl and propargyl imines leads to generation of N-1-alkylallyl-imines and propargyl analogs via α-alkylation of intermediate anions. Finally, the stereochemistry of azadiene formation has been probed by use of the conversion of N-(1-triethylsilylpropen-1-yl) benzaldimine to 1-phenyl-2-aza-1,3-pentadiene. Solvent, water concentration and a metal cation complexing agent all appear to influence the stereoselectivity of this process.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
