Tert-butyl phenyl ketone

SECONDARY AND TERTIARY ALKYL KETONES FROM CARBOXYLIC ACID CHLORIDES AND LITHIUM PHENYLTHIO(ALKYL)CUPRATE REAGENTS tert-BUTYL PHENYL KETONE... 

AT7C CONI CiiHi40 tert-butyl phenyl ketone 1XVR CBHgC0C(CH3)3 EtOH IL BARB 0.03 Bu4N+ 0.2 BARB 0.1C Bu4N+ 0.2 A H 20 DME/SCE 12A0 C=1.00... 

B, giving the (S)-enantiomer as the major product. However, there is a delicate balance between electronic and steric factors. Hence, the decrease in enantiose-lectivity seen in the reduction of tert-butyl phenyl ketone reflects greater steric interactions in transition state A between the Al-O bond and the tert-butyl group. 

Traditionally cyanohydrins have been prepared by processes that require the establishment of an equilibrium between a ketone and its corresponding cyanohydrin. For many ketones, especially those that are sterically hindered, the position of the equilibrium is unsatisfactory for the effective synthesis of the cyanohydrin. We describe herein a general method for the synthesis of cyanohydrins which does not depend on an equilibrium process. As a result this synthetic procedure can be used to convert a wide variety of dialkyl, diaryl, and arylalkyl ketones into their corresponding cyanohydrins. In addition to the described conversion of benzophenone into its cyanohydrin, acetophenone, fluorenone, tert-butyl phenyl ketone, and a wide variety of aliphatic ketones have been converted into cyanohydrins by this general procedure (Table... 

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