Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents

Abstract

[Bis(trifluoroacetoxy)iodo]benzene (BTI) and (diacetoxyiodo)benzene (DIB) efficiently promote the formation of acylnitroso species from hydroxamic acids in the presence of various dienes to give the corresponding hetero-Diels–Alder (HDA) adducts in moderate to high yields. The present method could be applied to the HDA reactions of acylnitroso species with o-benzoquinones generated by the oxidative dearomatization of guaiacols.

Keywords

• acylnitroso
• benzoquinone
• cycloaddition
• dearomatization
• iodine(III)