Name Reactions in Organic Chemistry by Alexander R. Surrey (Auth.)

By Alexander R. Surrey (Auth.)

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Soc. 55, 3475 (1933). 32 Von Braun Degradation A m e t h o d of r u p t u r i n g a C - N b o n d in a tertiary amine b y reaction w i t h cyanogen b r o m i d e is known as t h e von Braun d e g r a d a t i o n . T h e b r o m i n e becomes attached to t h e carbon atom, a n d t h e cyano group to the nitrogen. An intermediate complex is p r o b a b l y involved which decomposes to give t h e cyanamide a n d alkyl bromide. 1 R N + BrCN [R NCN] Br~ > R NCN + RBr + 3 3 2 W i t h unsymmetrical tertiary amines t h e products are determined by t h e n a t u r e of the substituents involved.

Degree from the University of Copenhagen. , in 1923. Six years later, after a disastrous fire, the company was purchased by the Monsanto Chemical Company, and Clemmensen joined the research staff in the department headed by L. R. Kyrides. Some of his work there included the preparation of alkyl and aryl phosphates and thiophosphates. In 1933, he founded the Clemmensen Chemical Corporation in Newark, New York, and held the position of president of that company until his death. T h e conversion of a carbonyl group to a methylene group by means of a m a l g a m a t e d zinc a n d hydrochloric acid is known as the Clemmensen m e t h o d of r e d u c t i o n .

6. For reductions by lithium aluminum hydride, see W. G. Brown, in "Organic Reactions" (R. ), Vol. VI, p. 469. Wiley, New York, 1951. 7. For a review of catalytic hydrogenation of esters to alcohols over a copperchromic oxide or Raney nickel catalyst, see H. Adkins, in "Organic Reactions" (R. ), Vol. VIII, p. 1. Wiley, New York, 1954. 28 Bouveault Aldehyde Synthesis T h e reaction of Grignard reagents with disubstituted formamides was shown by Bouveault to give aldehydes. 1 RMgX + R'R"NCHO » RCHO + R'R"NH + MgX T h e main side reaction in this synthesis is the formation of tertiary amines according to the following equation: 2 2RMgX + HCONR'R" *> R CHNR'R" + MgO + MgX, Smith and co-workers ' have investigated the use of Grignard reagents in t h e preparation of aldehydes.

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