t-RNH2—•t-RNH-R'
t-RNH 2 +R'CHO—-t-RN=CHR / t-alkyl aldimine
1
Amino-Hydrogen Substitution
of a t-Alkyl Amine. In many such reactions, why is a secondary amine obtained readily, with little formation of
2 Reaction with Aldehydes. Do t-alkyl amines and straight-chain amines give similar products when reacted with aldehydes?
tertiary amine?
3 Oxidation to Nitro Derivatives. Can both t-alkyl amines and straight-chain amines be readily oxidized to nitro derivatives?
R N H 2 — -RNO2
4 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?
Gl2 NaON t-RNH2 — • [t-RNHCI] — t-RNH-CN NaOH
t-Alkyl Amine Quiz—with answers worth knowing... Steric-controlled reactivity, provided by the attachment of 1 ammo 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 tertiarv 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.
2 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. 3 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 tertiarv nitroDarafRns. 4 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, Menthane Diamine. 18
C&E N
ROHIVI & HA AS P H I L A D E L P H I A
5, PA.
B
