The New Jersey Institute of Technology's
Electronic Theses & Dissertations Project

Title:	Synthesis of strained bridgehead lactams
Author:	Tu, Quansing
View Online:	njit-etd1988-049 (ii, 63 pages ~ 3.1 MB pdf)
Department:	Department of Chemical Engineering, Chemistry and Environmental Science
Degree:	Master of Science
Program:	Chemistry
Document Type:	Thesis
Advisory Committee:	Greenberg, Arthur (Committee chair) Venanzi, Carol A. (Committee member) Kebbekus, Barbara B. (Committee member)
Date:	1988-05
Keywords:	Lactams
Availability:	Unrestricted
Abstract:	While 1-Azabicyclo(3,3,1)nonan-2-one was originally thought to be difficult to synthesize, two different methods (DCC and di-n-butyltin oxide) will produce it with high yield. DCC is a strong reagent for absorbing water; the di-n-butyltin oxide method uses a Dean-Stark to remove water and is very useful. Bredt's rule influences the synthesis and stability of the N-bridgehead bicyclic lactams, this is apparent in the lactam series in the behavior of the (2,2,2) compounds and the (3,2,1) compound which we tried unsuccessfully to synthesize.