Water induces a change in the product of radical multifunctionalization reactions of aliphatic alkenes involving an sp3 C–H functionalization by an 1,5-hydrogen shift using tert-butyl nitrite and molecular oxygen. The reaction without water, reported previously, gives nitrated γ-lactols, whereas the reaction in the presence of water produces 4-hydroxy-5-nitropentyl nitrate or 4-hydroxy-3-nitropentyl nitrate derivatives.
水诱导了脂肪烯自由基多功能化反应中产物发生变化,涉及通过1,5-氢位移使用
叔丁基硝酸酯和分子氧进行的sp³ C-H功能化。之前报道的无
水反应会生成硝化的γ-乳醇,而在有
水存在下的反应则产生
4-羟基-5-硝基戊基
硝酸酯或
4-羟基-
3-硝基戊基
硝酸酯衍
生物。