A m ï n o - H y d r o g e n Substitution (e.g. Alky la* t i o n , cyanoethylation, carboxyethylation). Sec* ondary amines f o r m e d , but " s t e r i c c o n t r o l " retards tertiary amine f o r m a t i o n . t-RNH2
•- t - R N H - R '
Straight-chain amines give a mixture of secondary and tertiary amines. R e a c t i o n with A l d e h y d e s . t-RNHa + R'CHO
•- t - R N = CHR' stable aldimine
Straight-chain amines and aldehydes normally give unstable derivatives. Oxidation. t-RNH2
KMn04 •• t - R N O s
Straight-chain amines give complex, u n p r e dictable products. P r e p a r a t i o n off t - A l k y l c y a n a m i d e s . Cl2
NaCN •- [ t - R N H C l ] • t-RNH-CN NaOH W i t h straight-chain amines, this reaction requires close control, since t h e cyanamides react f u r t h e r in alkaline medium t o f o r m c o m plex p r o d u c t s .
t-RNHa
Rohm & Haas
t-ALKYL AMIN foresterie Controlled" reactivity In many reactions, t-alkyl primary amines show unusual reactivity not exhibited by the straight-chain isomers. Why ?—"Steric Control", resulting from the attachment of the amino group to a tertiary carbon in the t-alkyl amines makes the big difference. Four reactions that demonstrate the effect of this structural difference are given at the left. Why not explore further the potential of these amines? Write to Dept. SP-16 for samples and a M-page book giving many more t-alkyl amine reactions.
ROHM & H A A S t - A L K Y L A M I N E S P r i m e n e 8 1 - R : 12-14 carbon t-alkyl primary amine P r i m e n e J M - T : 18-22 carbon t-alkyl primary amine t-Butylamine t-Nonylamine t-Octylamine Menthane Diamine PRIMENE is a trademark, Reg, U.S. Pat, Off, and in principal
foreign countries.
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