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Author: Subject: Product of tert-butanesulfinyl ketimines
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[*] posted on 17-8-2017 at 05:17
Product of tert-butanesulfinyl ketimines


If you take a tert-butanesulfinyl ketimine, reduce it with NaBH4 and then cleave the suflinyl group via hydroylsis, is a primary or secondary amine produced?

The original Ellman paper suggests a primary amine, but other sources indicate that tert-butanesulfinyl ketimines produce secondary amines and tert-butanesulfinyl aldimines produce primary amines.
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[*] posted on 17-8-2017 at 08:47


Ketimine --> primary amine with secondary carbon
Aldimine --> primary amine with primary carbon
see attached scheme.

untitled.png - 15kB
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