Dithiolate Anions Turning Things Upside Down

Dithiolate Anions Turning Things Upside Down - Dithiolate...

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Dithiolate Anions: Turning Things Upside Down A very interesting bit of chemistry will allow us to turn around the fundamental electrophilic nature of the carbonyl and make it a nucleophile. As we know, the partial positive charge of the carbonyl carbon is an electrophile and attracts all types of nucleophiles. O ! ! Normal Electrophilic Behavior MgCl Li H HO It would be both interesting and useful to be able to turn this behavior around and make this carbon a nucleophile. This looks crazy but bear with me. H O + R Br R O + H + Br Crazy Stuff This looks crazy but it can be done by temporarily changing the carbonyl to something else that expresses different reactivity and then change it back after the reaction. Just like protection-deprotection but just the opposite. Making a Carbonyl Carbon Electrophilic: How it is Done. In order to use the carbonyl carbon as a nucleophilic anion, we are going to disguise it temporarily as a dithioacetal (the sulfur analogue to a normal acetal). Acetal
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This note was uploaded on 09/25/2009 for the course CH 223 taught by Professor Brown during the Summer '08 term at N.C. State.

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Dithiolate Anions Turning Things Upside Down - Dithiolate...

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