Alkyl-2,3-epoxypropylamines

An improved procedure yielded new alkyl-2,3-epoxypropylamines ( 2 ), ranging from very unstable (n-alkyl) to exceptionally stable (t-alkyl)types. Kinetics and other data relating to the stabilities of 2 are discussed. Cyclodimerization of 2 gave 1,5-disubstituted-1,5-diazacycloo¨ctane-3,7-diols ( 4 ). An alternative synthesis, which also yielded 4 with unlike substituents, employed diglycidylamines and primary amines. Conformational factors in these novel ring closures are discussed. Condensations of diglycidylamines with sulfide ion gave substituted 1-aza-5-thiacycloo¨ctane-3,7-diols ( 5 ).