Answers are grounded in this paper and cite their sources.
The regiochemistry of the intramolecular Schmidt reaction of 2-azidoalkylketones is controlled by placing a thioether substituent at the position adjacent to the ketone to provide access to a family of unsubstituted medium bridged twisted amides. This outcome is ascribed to the presence of stabilizing through-space interactions between the diazonium cation and the n electrons on heteroatom and does not require a locked conformation of the ketone.
No takes yet. Share an insight, caveat, or question.
Szostak et al. (2009) studied this question.
Synapse has enriched 10 related papers. Consider them for comparative context: