Preparation and functionalization of regioselectively substituted pyrroles/

Abstract

The reaction of 1-substituted vinamidinium salts with sarcosine ethyl ester produced 2,3-disubstituted pyrroles; a similar reaction with glycine ethyl ester gave 2,5-disubstituted pyrroles. Reactions of 3-aryl-3-chloro propeniminium salts, 1-aryl vinamidinium salts, 1-aryl- 3-(dimethylamino)-2-propenone, 3-chloro-3-aryl-2-propenal and 3-aryl-3-(dimethylamino)-2-propenal with sarcosine and glycine were studied under basic, neutral and acidic conditions. The best conditions to make pyrroles are with 3-aryl-3-chloropropeniminium salts and 1-aryl vinamidinium salts under basic conditions, which were the initial conditions reported. A number of previously prepared 2,4-disubstituted pyrroles were brominated, and most dibrominated readily. The pyrroles with strong electron withdrawing groups were more difficult to brominate and only monobromination was observed.

Notes

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Graduation Date

1993

Semester

Summer

Advisor

Gupton, John T.

Degree

Master of Science (M.S.)

College

College of Arts and Sciences

Department

Chemistry

Format

PDF

Pages

146 p.

Language

English

Length of Campus-only Access

None

Access Status

Masters Thesis (Open Access)

Identifier

DP0028681

Subjects

Arts and Sciences -- Dissertations, Academic; Dissertations, Academic -- Arts and Sciences

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