Date of Award
Master of Science (MS)
R. L. Dressler
This research involved an attempt to synthesize 3,4-dihydrocarbostyril by electrophilic substitution involving a nitrenium ion. Preparation of 3,4-dihydrocarbostyril was reported in 1937, having been synthesized by the Schmidt reaction using 1-indanone and hydrazoic acid in sulfuric acid-benzene solution. Cyclization of N-bromohydrocinnamamide has been investigated using silver nitrate in 9.5% ethanol, and silver acetate in glacial acetic acid: both gave unsatisfactory results. When a solution of silver tetrafluoroborate in nitromethane reacted with N-bromohydrocinnamamide, the product obtained did show substantial evidence by infrared, nuclear magnetic resonance and mass spectrometry that the desired product was formed.
Copyright 1976 Ataolah Shirazi
Shirazi, Ataolah, "A Study of a Ring Formation Via a Nitrenium Ion Intermediate" (1976). Master's Theses. 1638.