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The reaction of N-benzyloxypyridinium bromide with sodium borohydride: Mechanistic aspects

✍ Scribed by R.E. Manning; F.M. Schaefer

Publisher
Elsevier Science
Year
1974
Tongue
French
Weight
157 KB
Volume
15
Category
Article
ISSN
0040-4039

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✦ Synopsis

The reduction of N-alkyl pyridinium salts with sodium borohydride is a well-known reaction, yielding in most cases the corresponding 1, 2, 3, C-tetrahydropyridine derivatives.

1 The mechanistic aspects of this reaction have been studied and a mechanism proposed. 2 We wish to report our studies on the analoguous reduction of N-benzyloxy pyridinium bromides. The literature describes one example of this reaction; the reduction of N-methoxy pyridinium perchlorate to pyridine. 3 Subsequent to completion of our work, the reduction of N-alkoxy pyridinium salts has been reported to yield a mixture of the corresponding tetrahydro pyridine, pyridine and piperidine ds rivatives. 4 In our studies, we have found that treatment of simple N-benzyloxy pyridinium bromides with sodium borohydride affords as the major products the corresponding tetrahydropyridines and bensylalcohol. (e.g. I -b II and III)

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