Sciencemadness Discussion Board

Product of tert-butanesulfinyl ketimines

benzoyl - 17-8-2017 at 05:17

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.

Sigmatropic - 17-8-2017 at 08:47

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

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