Reduction of Pyridyl Carbinols with Sodium Borohydride/Trifluoroacetic Acid

CF Nutaitis, TJ Greshock, SR Houghton…

Index: Nutaitis, Charles F.; Greshock, Thomas J.; Houghton, Stephen R.; Moran, Lynn N.; Walter, Melissa A. Organic Preparations and Procedures International, 2002 , vol. 34, # 3 p. 332 - 335

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Citation Number: 6

Abstract

As can be seen in the Table, carbinols at all three positions of the pyridine ring are susceptible to reduction. Furthermore, the reduction pattern parallels that of the previously reported 1, 3-azoles-that is, two additional aromatic or heteroaromatic rings are required for stabilization of the intermediate carbocation and hence reduction of the carbinol to the corresponding methane. The last entry in the Table, which possesses only one additional ...

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