A Study of a Ring Formation Via a Nitrenium Ion Intermediate

Author

Ataolah Shirazi, Fort Hays Kansas State College

Document Type

Thesis - campus only access

DOI

10.58809/JNBT4844

Date of Award

Summer 1976

Degree Name

Master of Science (MS)

Department

Chemistry

Advisor

R. L. Dressler

Abstract

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.

Comments

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Recommended Citation

Shirazi, Ataolah, "A Study of a Ring Formation Via a Nitrenium Ion Intermediate" (1976). Master's Theses. 1638.
DOI: 10.58809/JNBT4844
Available at: https://scholars.fhsu.edu/theses/1638

Rights

© 1976 Ataolah Shirazi