Ghirardelli, Robert George (1956) I. The stereochemistry of the opening of the imine ring with various reagents. II. The attempted reduction of naturally occuring threonine to 3-amino-2-butanol. Dissertation (Ph.D.), California Institute of Technology. http://resolver.caltech.edu/CaltechETD:etd-03232004-104542
The 2,3-iminobutanes react with acetic acid to give products that are easily converted without isolation into 3-acetamido-2-acetoxybutanes. Comparisons of the latter with samples of known configuration demonstrate that ring opening occurs in a trans manner.
Attempts to prepare 3-p-toluenesulfonamido-2-p-toluenesulfonoxybutane by reaction of 2,3-iminobutane with p-toluenesulfonic acid, followed by treatment with p-toluenesulfonyl chloride, have failed. Under mild conditions the ring is not attacked, and under strenuous conditions elimination of ammonia occurs.
The ring of the N-ethyl-2,3-iminobutanes, as well as that of the simple 2,3-iminobutanes, is opened by aqueous ammonia and ethylamine at elevated temperatures to give products which demonstrate that an inversion occurs. Many new imines, amino alcohols, and diamines have been synthesized. They are described, along with some of their derivatives.
Both DL- and naturally occurring threonine have been reduced to derivatives of the corresponding 2-amino-1,3-butanediols. Attempts to reduce the latter to derivatives of the 3-amino-2-butanols have not yet succeeded.
|Item Type:||Thesis (Dissertation (Ph.D.))|
|Degree Grantor:||California Institute of Technology|
|Division:||Chemistry and Chemical Engineering|
|Thesis Availability:||Public (worldwide access)|
|Defense Date:||1 January 1956|
|Default Usage Policy:||No commercial reproduction, distribution, display or performance rights in this work are provided.|
|Deposited By:||Imported from ETD-db|
|Deposited On:||23 Mar 2004|
|Last Modified:||26 Dec 2012 02:34|
- Final Version
See Usage Policy.
Repository Staff Only: item control page