MOLECULAR REARRANGEMENTS. XVIII. THE DEAMINATION OF ERYTHRO-AND THREO-1- AMINO-1-PHENYL-2-p-TOLYL-2-PROPANOL

Journal Article · Fri Sep 01 00:00:00 EDT 1961 · Journal of the American Chemical Society (U.S.)

DOI:https://doi.org/10.1021/ja01478a026· OSTI ID:4840546

Benjamin, B M; Collins, C J

The deaminations of optically active erythro- and threo1-amino-1-phenyl- 2-p-tolyl-2-propanol (III) were studied. Whereas the erythro isomer yields p- methylbenzhydryl methyl ketone (IV) in which inversion predominates over retention in the ratio of 74: 26, the threo isomer produces in which the ratio of inversion to retention is 43:57. These data clearly establish the open carbonium character of the intermediates. The absence of alpha -phenyl-4'- methylpropiophenone (V) in either deamination product rules out methyl thigration during both reactions. (auth)

• Research Organization: Oak Ridge National Lab., Tenn.
• NSA Number: NSA-15-030648
• OSTI ID: 4840546
• Journal Information: Journal of the American Chemical Society (U.S.), Journal Name: Journal of the American Chemical Society (U.S.) Vol. Vol: 83; ISSN JACSA
• Country of Publication: Country unknown/Code not available
• Language: English

Related Subjects

ALKYL RADICALS
AMINES
CHEMISTRY
DEAMINATION
DECOMPOSITION
DIFFUSION
ETHYL RADICALS
ISOMERS
KETONES
METHYL RADICALS
MOLECULES
PHENYL RADICALS
PROPANOL
PROPIONIC ACID