Aziridinyl compounds rearrangement

Tsunoda et al. (73BCJ3499) have reported a novel reverse Smiles rearrangement of N,N- bis-(l,3,5-triazinyl)-2-aminophenols (Scheme 25). 2,4,6-Tris(l-aziridinyl)-l,3,5-triazine is rearranged by acid into the tetracyclic compound (40 equation 16) (55JA5922). 

V-acylaziridine-2-imides to oxazoline-4-imides, followed by hydrolysis of these latter compounds, has been used586 to afford chiral / -hydroxy-a-amino acid precursors. It has been suggested587 that the observed thermal rearrangement of c/.s-aziridinyl ketone tosylhydrazones (449) to 5-alkylamino-3,5-diphenyl-l-tosyl-2-pyrazolines (450) is... 

The development of a tandem rhodium-catalyzed Bamford-Stevens/thermal aliphatic Claisen rearrangement sequence was elegantly demonstrated by Stoltz. As a general method to prepare non-carbonyl-stabilized diazo compounds in situ, this group chose to investigate the decomposition of //-aziridinyl imines (also known as Eschenmoser hydrazones) 28. ... 

The reaction of geminal dibromides and carbonyl compounds in the presence of butyl-lithium or lithium metal can provide a general route to a wide range of oxirans. Stevens and Pillai have used a Darzens cyclization reaction to form the first example of an isolable epoxy-amine (121). 2-(l-Aziridinyl)-2-phenyl-l-oxaspiro[2,5]octane (121) was relatively stable and rearranged to the corresponding cycloheptanone (122) only after... 

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