The Synthesis of N-Chlorosulfonyl β-Lactams and Their Rearrangements

Author

Lihua Zhang, Eastern Illinois University

Degree Name

Master of Science (MS)

Semester of Degree Completion

1995

Thesis Director

T. Howard Black

Abstract

The synthesis of several N-chlorosulfonyl-β-lactams and their rearrangements have been carried out via CSI (chlorosulfonylisocyanate) reaction. The mechanism of β-lactam synthesis as well as its rearrangements were also studied. The characterization of β-lactams was performed with IR, ¹H and ¹³C NMR, and HRMS. β-lactams 2-chlorosulfonyl-1-methyl-2-azabicyclo[4.2.0]octan-3-one (71), 1-chlorosulfonyl-4-methyl-4- (phenylmethyl)azetidin-2-one (74) and 1-chlorosulfonyl-4,4- (diphenylmethyl)azetidin-2-one (75) were synthesized for the first time. β-lactam 4-chlorosulfonyl-3, 9, 9-trimethyl-4-azatricyclo [6.1.0.0^3,6] nonan-5-one (73) was obtained as crystalline solid instead of liquid.

Different effects, such as temperature, solvents and catalysts, on the rearrangement of the β-lactam 74 have been studied. There was no expected rearrangement to Γ-lactam observed, and usually the unsaturated amide resulted.

The rearrangement products of a β-lactam can be Γ-lactam, α,β- or β,Γ-unsaturated amide, and alkene, depending on the conformation of the β-lactam and reaction conditions.

Recommended Citation

Zhang, Lihua, "The Synthesis of N-Chlorosulfonyl β-Lactams and Their Rearrangements" (1995). Masters Theses. 1967.
https://thekeep.eiu.edu/theses/1967