3.7- DIMETHYL-1.6-OCTADIEN-3-AMINE

The reaction has been improved to a satisfactory process by modifying the reaction conditions. A remarkable effect of the addition of amines on the reaction was observed (49). For example, the reaction of butadiene (4 moles) and acetic acid (4 moles) in the presence of 2-(N,/V-dimethyl-amino)ethanol (4 moles) using Pd(acac)2 (3 mmoles) and PPh3 (3 mmoles) at 90°C gave complete conversion after 2 hours. The product was found to consist of 8-acetoxy-1,6-octadiene (47) (71%), 3-acetoxy-1,7-octadiene (48) (21%) and 1,3,7-octatriene (16) (8%). Various tertiary amines, such as triethylamine, )V-methylmorpholine, Af,Af,N, N -tetramethyl-1,3-bu-tanediamine, and triethylenediamine, showed the same favorable effect. Other basic salts, such as sodium and potassium acetate, accelerate the reaction, especially at high concentrations (50, 51). The selection of solvents is also important. Arakawa and Miyake found that electron-donating type solvents (e.g., THF and triethylamine) are good solvents... 

ALLYLICALLY TRANSPOSED AMINES FROM ALLYLIC ALCOHOLS 3,7-DIMETHYL-l,6-OCTADIEN-3-AMINE... 

Clizbe, L. A., Overman, L. E. Allylically transposed amines from allylic alcohols 3,7-dimethyl-1,6-octadien-3-amine. Org. Synth. 1978, 58, 4-... 

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