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Copy of Chapter 17

Thewolff kishne re r duction is an alte rnativeto

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Unformatted text preview: id) and thioace de tal sulfurization m thods e (incom patiblewith cat. H2- se nsitivegroups) of de oxyge nating alde s and ke s. hyde tone Usein alkylbe nesynthe nze sis: Br Br Br Br 4. Addition of Non-organometallic Carbon Nucleophiles a. C yanidem s cyanohydrins ake To make HCN HC N NaOH NaOH Mechanism: Use fulne C-Cbond form ss: ation with -C as a ve N rsatilefunctional group. b. TheWittig Re action Discove d during an inve re stigation of S 2 re actions of N phosphine with haloalkane s s. Ge Wittig org (18971987) NP 1979 Phosphoniumsalt synthe sis The chargeon P acidifie the s adjace C-H: De nt protonation give a so-calle ylide s d Nucle ophilic Vale she e nce ll xpande d Othe (we r) base OK, such as C 3O-, C 3OH, ge ratetheylidein e r ake s H H ne quilibrium conce ntrations sufficie for thene ste Attack on carbonyl carbon and form nt xt p: ation of alke s. ne Wittig Br C H Driving force Ve strong bond : ry C pare om : S roid m te odification O H H O H O C...
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