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New difluoromethylene templates and discovery of an alkynylogous aldol reaction through an allene-propargyl interconversion
Bo Xu
Paperback. ProQuest, UMI Dissertation Publishing 2011-09-02.
ISBN 9781243498953
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Förlagets beskrivning
Our research focus on developing the alkynylogous version of known reactions. The idea is simple: the reactivity of nucleophilic or electrophilic site in a molecule could be extended though triple bonds (alkynylogous extension), so the reaction may actually happen at a remote carbon through an allene-propargyl inter-conversion. We have two applications: (i) a highly regioselectively alkynylogous aldol reaction was developed; the size and Lewis acidity of the counterion of a base exerts a profound influence on regioselectivity. (ii) a de facto SN2 substitution reaction of difluoropropargyl bromide has been fulfilled through a sequential SE2' and S N2' Reactions. The structure and reactivity of the intermediate propargyl indium complex also has been investigated. Their reaction with electrophiles produced a difluoro-alkyne or --allene, depending on the nature of the electrophile. We have invoked a mechanism based on the Curtin-Hammett principle to explain this phenomenon
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New difluoromethylene templates and discovery of an alkynylogous aldol reaction through an allene-propargyl interconversion
Bokrecensioner » New difluoromethylene templates and discovery of an alkynylogous aldol reaction through an allene-propargyl interconversion
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