1,1-二苯基-2-硝基乙烯及其衍生物與格里納試劑反應,經稀酸水溶液水
解後得到屬於1,4-加成的產物o 例如一級的硝基烷類及 oxime 化合物;但
如果將反應所形成的intermediate-nitronate 加入強酸中,則進行 Nef
或 Meyer reaction, 預期為羰基或酸化合物,但在反應的過程中,卻意外
的捕抓住鹵素離子,而形成中間產物 hydroximoylhalides. hydroximoyl
halides 可和鹼作用脫去 HX 而生成 nitrile oxides. nitrileoxides
和烯或炔進行 1,3-dipolar cycloaddition 的反應,得到具有專一性或高
選擇性的 2-isoxazoline 或 isoxazole.由於立體障礙因素,使得
1,1,2-三苯基-2-硝基乙烯與三級丁基或二及異丙基等之立障較大之格里
納試劑反應時,改以自由基的方式進行反應,整個反應過程可知,苯基及烷
基扮演著相當重要的角色o

1,1-Diphenyl-2-nitroethylene and their derivatives can react
with Grignandreagents to form 1,4-addition products such as
primary nitroalkanes and oximes after workup with dilute aqueous
acid solution. On the other hand,if the intermediate-nitronates
are added to ice cold 85% H2SO4 or concentratedHX(aq) solution
will undergo Nef or Meyer reaction and the expected producted
are carbonyl compounds or carpoxylic acids. Surprisingly, the
hydroximoyl Halides are formed if the reactive intermediate trap
the halogen ions. Hydroximoyl halides will convert into nitrile
oxides in the presence of base.It is known that nitrile oxides
under 1,3-dipolar cycloaddition with alkenes oralkynes to
generate stereospecific or steroselective of 2-isoxalolines
orisoxazoles.1,1,2-Triphenyl-2-nitroethylene react with Grignard
reagents to give free radical or SET products if the
organomagensium halides belong to teritary orsecondary reagents.
the different results can be ascribed to the steric effectof the
phenyl and bulky alkyl groups.
1,1-Diphenyl-2-nitroethylene and their derivatives can react