Collins, SG,O'Sullivan, OCM,Kelleher, PG,Maguire, AR

2013

January

Organic & Biomolecular Chemistry

Design and synthesis of stable alpha-diazo-beta-oxo sulfoxides

Validated

()

C-H INSERTION METAL CARBENE TRANSFORMATIONS NUCLEAR-MAGNETIC-RESONANCE ORGANIC-SYNTHESIS DIAZOCARBONYL COMPOUNDS SULPHONYL AZIDE S-OXIDES 1,4-OXATHIAN-2-ONES DIAZOSULFOXIDES CHEMISTRY

11

1706

1725

Diazo transfer adjacent to a sulfoxide moiety to provide stable, isolable alpha-diazo-beta-oxo sulfoxides has been achieved. Use of monocyclic and bicyclic sulfoxide precursors is critical in enabling isolation of stable derivatives, through introduction of conformational constraint, while acyclic alpha-diazo-beta-oxo sulfoxides are too labile to isolate and characterize.

DOI 10.1039/c3ob27061k