Correlation of the Product E/Z Framework Geometry and O/O vs O/N Regioselectivity in the Dialkylation of Hyponitrite

摘要: The products from the alkylation of silver hyponitrite with tert-butyl bromide, tert-amyl p-tert-butyl benzylbromide, and chlorotriethylsilane have been determined. In reaction bromide formation three new products, namely, (Z)-N-tert-butyl-N‘-tert-butoxydiazene-N-oxide {(CH3)3CN(O)NOC(CH3)3}, 1D, trans-mono-O-tert-butylhyponitrous acid {(CH3)3CONNOH}, 2A, (Z)-N-tert-butyl-N‘-hydroxydiazene-N-oxide {(CH3)3CN(O)NNOH}, 2D, is observed together known trans-di-O-tert-butyl {(CH3)3CONNOC(CH3)3}, 1A. also yielded corresponding derivatives. However, reactions p-tert-butylbenzyl hyponitrite, trans-di-O-tert-alkylhyponitrites were obtained as only alkylated products. differential reactivity two sets halides explained in terms higher stability cations generated...