1220339-83-2Relevant academic research and scientific papers
Synthetic and mechanistic studies of the aza-retro-claisen rearrangement. a facile route to medium ring nitrogen heterocycles
Boeckman Jr., Robert K.,Genung, Nathan E.,Chen, Ke,Ryder, Todd R.
, p. 1628 - 1631 (2010)
An efficient synthesis of medium-sized heterocyclic rings was achieved using a one-pot aza-Wittig/retro-aza-Claisen sequence of vinyl cyclobutanecarboxaldehydes derived from simple allylic carbonates. The use of various Staudinger reagents in the aza-Wittig reaction allows for a variety of N-substituted products to be obtained. The rearrangement is under thermodynamic control driven by relief of the cyclobutane ring strain and resonance stabilization of the resulting vinylogous amide/sulfonamide.
