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
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
STARS Citation
Smith, Lana L., "Preparation and functionalization of regioselectively substituted pyrroles/" (1993). Retrospective Theses and Dissertations. 3742.
https://stars.library.ucf.edu/rtd/3742