Hoch-Campbell ethylenimine synthesis

In organic chemistry the Hoch-Campbell ethylenimine synthesis is a method for constructing ethyleneimines from oximes. The oxime is treated with Grignard reagents: ^{[1] [2] [3] [4]}

Hoch-Campbell Ethylenimine Synthesis

The above product is called 3-methyl-2,2-diphenylaziridine [7764-13-8]. A compound that is described is called 2-amino-1,1-diphenylpropan-1-ol [57728-35-5]. This is an open-chain analog of pipradrol. 99% of the theoretical yield can be achieved by Grignard addition of two equivalents of phenylmagnesium bromide to alanine ethyl ester.

N.B. Joseph Hoch was the first chemist to invent diphenylacetonitrile.

References

1. (a), Hoch, Compt. rend., 196, 1865 (1934); (b), ibid., 203, 799 (1936); (c), ibid., 204, 358 (1937).
2. Kenneth N. Campbell; James F. Mckenna (1939). "The action of Grignard reagents on oximes. i. The action of phenylmagnesium bromide on mixed ketoximes". Journal of Organic Chemistry . 4 (2): 198–205. doi:10.1021/jo01214a012.
3. Kenneth N. Campbell; Barbara Knapp Campbell; Elmer Paul Chaput (1943). "The reaction of Grignard reagents with oximes. ii. The action of aryl grignard reagents with mixed ketoximes". Journal of Organic Chemistry . 8 (1): 99–102. doi:10.1021/jo01189a015.
4. Kenneth N. Campbell; Barbara K. Campbell; James F. Mckenna; Elmer Paul Chaput (1943). "The action of Grignard reagents on oximes. iii. The mechanism of the action of arylmagnesium halides on mixed ketoximes. A new synthesis of ethyleneimines". Journal of Organic Chemistry . 8: 103–9. doi:10.1021/jo01189a016.