Theses and Dissertations

Hua Guo

Issuing Body

Mississippi State University

Advisor

Pittman Jr., U. Charles

Committee Member

Sygula, Andrzej

Committee Member

Foster, C. Stephen

Date of Degree

8-9-2008

Document Type

Graduate Thesis - Open Access

Major

Chemistry

Degree Name

Master of Science

College

College of Arts and Sciences

Department

Department of Chemistry

Abstract

Three types of 2-alkenylthiazolines were designed and synthesized by a two-step method starting with 2-methylthiazoline and aromatic aldehydes, alkyl aldehydes and alkenyl aldehydes, respectively. Diels-Alder reactions of several 2-styryl-1,3-thiazolines with maleic anhydride in toluene were attempted. Expected Diels-Alder products were not observed or separated. Only starting materials were recovered. Several 2-alkenyl-1,3-thiazolines were successfully reacted with benzoyl chloride to form the N-benzoyl mono-substituted products. This is in sharp contrast with the di-benzoylation of 2-methylthiazoline reported previously by the Pittman group. 2-Methylbenzothiazole was reacted with different folds of aroyl chlorides. However, only di-aroylation products were observed even when a 1:1 2-methylbenzothiazole:aroyl chloride ratio was employed. Finally, N-methyl cyclic ketene N,O- and N,S-acetals were reacted with different alkylsulfonyl chlorides, respectively. Only di-substituted products were found in the N,O-acetal reacitons and only mono-substituted products were found in the N,S-acetal reactions even when different folds of sulfonyl chloride was employed.

URI

https://hdl.handle.net/11668/15458

Comments

acylation||2-alkenylthiazolines||Organic synthesis

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