t-RNH2
t-RNH-R'
î-RNH 2 -hRCHO—-t-RN=CHR' t-alkyl aldimine
j 1 j Amino-Hydrogen Substitution of a t-Alkyl Amine. I n many such reactions, why is a secondary amine obtained readily, with little formation of tertiary amine?
2 j Reaction with Aldehydes. Do :-alkyl amines and straight-chain amines give similar products when reacted with aldehydes?
I 3 | Oxidation to Nitro Derivatives. Can both t-alkyl amines and straight-chain amines be readily oxidized to nitro derivatives?
Preparation of t-Alkylcyanamides. In this reaction, would you expect a higher yield if you used a t-alkyl amine instead of a straightchain amine?
RNH,
[0]
RN02
t-RNH, — • [t-RNHCI] — ! t-RNH-GN NaOH
t-Alkyl Amine Quiz—with answers worth knowing... m Steric-controlled reactivity, provided by the attachment of amino group to a tertiary carbon, permits one amino hydrogen to be substituted easily but retards tertiary amine formation. Similar reactions with straight-chain amines give mixtures of secondary and tertiary amines.
Write to Dept. SP-12 for samples and a 44-page book giving many r e a c t i o n s of t-alkyl amines.
No. t-Alkyl amines react with many alkyl and aromatic aldehydes to form stable aldimines, also called Schiff bases. Straight-chain amines and aliphatic aldehydes normally give unstable derivatives. No. t-Alkyl amines are unaffected by a variety of oxidizing agents which break up straight-chain amines to form complex, unpredictable products. When oxidized with a suitable reagent such as potassium permanganate, however, t-alkyl amines undergo clean reactions to tertiary nitroparaffins. Yes. With straight-chain aliphatic amines, this reaction requires close control, since the cyanamides react further in alkaline medium to form isomelamines or substituted guanidines. t-Alkylcyanamides are stable in the presence of a base. Rohm & Haas t-alkyl amines: PRIMENE* 81 R (12-14 carbons), PRIMENE JM-T (18-22 carbons), t-Butylamine, t-Octylamine, t-Nonylamine, Menthane Diamine.
ROHM HAAS &
P H I L A D E L P H I A
5, PA.
Circle No. 8 on Readers' Service Card
VOL. 53, N O . 3
·
MARCH 1961
89 A
