I. Attempted Violations of the Rule of Trans-nucleophilic Addition. Ii. Metalation and Alkylation of Mercaptals
Abstract
Previous work from this Laboratory¹ has shown thatnucleophiles add to negatively substitued acetylenes in a trans- manner. This study was initiated to further test the generality of this rule. Structures in which either steric or electronic factors favored a violation to the rule were investigated and in all cases the dominant mode of addition was in a trans manner. The chemistry of some of the substituted olefinic products resulting from addition was also investigated. A novel isomerization of B-arylmercaptoacrylic esters was found. Compounds of the type (I) in the presence of thiolate were found to undergo exchange of the RS- group and form.
Degree
Ph.D.
Subject Area
Organic chemistry
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