1,6‐Oxido[10]Annulene

Abstract

1,6‐Oxido[10]Annulene solvent: 50 ml. of petroleum ether intermediate: 11‐oxatricyclo[4.4.1.0 1,6 ]undeca‐3,8‐diene intermediate: 117 g. (0.250 mole) of finely powdered 3,4,8,9‐tetrabromo‐11‐oxatricyclo[4.4.1.0 1,6 ]undecane product: 1,6‐oxido[10]annulene

The synthesis of water soluble decalin-based thiols and S-nitrosothiols—model systems for studying the reactions of nitric oxide with protein thiols

“…Epoxy bis-alkene 13 was prepared from naphthalene by Birch reduction (Na-NH 3 ; 74%) then epoxidation (CH 3 CO 3 H; 87%). 33,34 Ring-opening of this epoxide with benzylthiol in ethylene glycol 35 afforded thioether bisalkene 14a (78%). The plan was to chemo-and stereoselectively oxidise this thioether bis-alkene to the corresponding bisepoxide using the axial tert-alcohol at C10 to direct epoxidation onto the a-face.…”