Isonitriles 1.1.3.3- tetramethylbutyl

N-( 1-butyl-lithium, 1,1,3,3-tetramethylbutyl isonitrile, and deuterium oxide,... 

Tetramethylbutyl isonitrile, from N-( 1,1,3,3-tetramethy lbutyl)-for-mamide and thionyl chloride, 51, 31... 

Isonitriles are presumed to be toxic, and it is recommended that the workup procedure be performed in a hood. Unlike most isonitriles, however, 1,1,3,3-tetramethylbutyl isonitrile is not malodorous. It has a sweetish pine odor, which becomes unpleasant only after continued inhalation. 

Aldehydes from 1,1,3,3-Tetramethylbutyl isonitrile and Organometallic Reagents... 

A. 1,1,3,3-Tetramethylbutyl isonitrile. A 3-1. three-necked round-bottomed flask is fitted with a Hershberg stirrer, a fiOO-ml. pressure-equalizing addition funnel, and a nitrogen gas... 

The molar amount of 1,1,3,3-tetramethylbutyl isonitrile used is equivalent to the Grignard reagent content. 

To palladium acetate (1.8 mg, 7.8 //mol) placed in a Schlenk-type tube under a nitrogen atmosphere is added 1,1,3,3-tetramethylbutyl isocyanide (16.8 mg, 0.12 mmol) under stirring at rt. >eep red color is observed immediately, indicating the formation of active palladium(0)-isonitrile catalyst. To the mixture successively added at rt are toluene (0.1 mL), (dimethylphenylsilyl)(pinacolato)borane (102 mg, 0.39 mmol), and 3-(/er/-butyldimethylsilyloxy)-l-propyne (91 mg, 0.53 mmol). The resulting mixture is heated to reflux for 1-4 h, then cooled down to rt, and finally subjected to a short column chromatography on silica gel (diethyl ether) to remove the catalyst. Further purification by bulb-to-bulb distillation of the crude product gives the title compound in 83% 3deld. 

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