t-RNH 2 +R / CH0—•t-RN=CHR /
t-RNH2—•t-RNH-R'
t-alkyl aldimine
j 1_J Amino-Hydrogen Substitution of at-Alkyl Amine. In many such reactions, why is a secondary amine obtained readily, with little formation of tertiary amine?
2 1 Reaction with Aldehydes. Do alkyl amines and straight-chain amines give similar products when reacted with aldehydes?
I 3 j Oxidation to Nitro Dériva tives. Can both t-alkyl amines and straight-chain amines be readily oxidized to nitro derivatives?
Preparation of t-Alkyl· cyanamides. In this reaction, would you expect a higher yield if you used a t-alkyl amine instead of a straightchain amine?
[0]
Gl2 NaCN t-RNH2 — • [t-RNHCI] — t-RNH-CN NaOH
RNH2
RN02
t-Alkyl Amine Quiz—with answers worth knowing. 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. 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. Circle No. 8 on Readers' Service Card 98 A
INDUSTRIAL AND ENGINEERING CHEMISTRY
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.
ROHM
HA&AS P H I L A D E L P H I A
S.PA,
