New data on the Hofmann reaction communication 4. Action of hypobromite on diastereoisomerig 3-(acylamino)-4-ethyloctanamide3

Summary

• 1. A study was made of the action of hypobromite on the diastereoelsomers A₁ and A₂ of 3-benzamido-and 3-(alkoxycarbonylamino)-4-ethyloctanamides.

• 2. From the products obtained from the benzamide compounds, the stereolsomeric 4-(1-ethypentyl)-2-imidazolidinones and 1-benzoyl-5-(1-ethylpentyl)-2-imidazolidinones and also benzoic acid, were isolated.

• 3. From the products obtained from the alloxycarbonylamino compounds, the stereoisomeric 1-alkoxy-carbonyl-5-(1-ethylpentyl)-2-imidazolidinones, 4-(1-ethylpentyl)-2-imidazolidinones, and 5-(1-ethylpentyl)-hydantoins, and also 2-ethylhexanoic acid, were isolated. When the oil remaining after the separation of the above compounds was hydrolyzed, hydrogen cyanide, ammonia, and 2-ethylhexanal were present among the products.

• 4. The results obtained confirm the correctness of the scheme that we have proposed previously for the Hofmann reaction with amides of acylatedβ-amino acids.