Indium triflate-assisted nucleophilic aromatic substitution reactions of nitrosobezene-derived cycloadducts with alcohols.
Exclusive nucleophilic aromatic substitution of hydrogen in conjunction with cleavage of the N-O bond was observed when nitrosobenzene-derived nitroso cycloadducts were treated with indium triflate in the presence of alcohols. Aromatic alkoxylated syn-1,4 aminocycloalkenol products with good to excellent regioselectivity (16:84 to 0:100, ortho:para) were obtained.
Yang
Baiyuan
B
Department of Chemistry and Biochemistry, 251 Nieuwland Science Hall, University of Notre Dame, Notre Dame, Indiana 46556, USA.
Miller
Marvin J
MJ
D000438:Alcohols / Q000737:chemistry*; D003500:Cyclization; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D008698:Mesylates; D009574:Nitro Compounds; C012077:trifluoromethanesulfonic acid