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首页> 外文期刊>Organic & biomolecular chemistry >In the first proven S_N2′ fullerene reaction, both C_3 and C_1 C_(60)F_(36) hydrolyse to C_1 isomers of C_(60)F_(35)OH that eliminate HF to give epoxides C_(60)F_(34)O; C_(60)F_(36)O oxides are shown to be ethers, and a fourth isomer of C_(60)F_(36) exi
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In the first proven S_N2′ fullerene reaction, both C_3 and C_1 C_(60)F_(36) hydrolyse to C_1 isomers of C_(60)F_(35)OH that eliminate HF to give epoxides C_(60)F_(34)O; C_(60)F_(36)O oxides are shown to be ethers, and a fourth isomer of C_(60)F_(36) exi

机译：在第一个证明的S_N2'富勒烯反应中，C_3和C_1 C_（60）F_（36）均水解为C_（60）F_（35）OH的C_1异构体，这些异构体消除了HF，得到环氧化物C_（60）F_（34）O ; C_（60）F_（36）O氧化物显示为醚，C_（60）F_（36）exi的第四种异构体

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摘要

On standing in organic solvents containing traces of water, C_3 and C_1 isomers of C_(60)F_(36) slowly convert to C_1 isomers of C_(60)F_(35)OH. Both fluorofullerenols eliminate HF during EI mass spectrometry to give C_(60)F_(34)O epoxides, one fullerenol being much less stable than the other to the extent that the mass spectrum shows only the epoxide. Both C_(60)F_(35)OH isomers have C_1 symmetry, one being identified by the remarkable linear relationship between chemical shifts in its ~(19)F NMR spectrum and those in the spectrum of C_1 C_(60)F_(36); the spectrum of the other shows the pattern of C_3 C_(60)F_(36) rendered asymmetrical by the replacement of one F by OH. The reactions are facilitated by the presence of isolated double bonds, and provide the first proven examples of an S_N2′ reaction of a fullerene derivative. Our observation explains why only a limited number of fluorines are readily replaced in C_(60)F_(36) and why C_(60)F_(18) is by contrast much more resistant to hydrolysis. We have isolated also a pure isomer of C_(60)F_(36)O, which is shown to be an oxahomofullerene (ether) apparently derived from C_1 C_(60)F_(36), and an impure fraction comprising a fourth isomer of C_(60)F_(36), a trifluoromethyl derivative of C_(60)F_(36), a second isomer of C_(60)F_(36)O, and an unknown species of 1392 u.
机译：在含有痕量水的有机溶剂中静置后，C_（60）F_（36）的C_3和C_1异构体缓慢转化为C_（60）F_（35）OH的C_1异构体。两种氟富勒烯醇在EI质谱分析中都消除了HF，得到C_（60）F_（34）O环氧化物，一种富勒烯醇的稳定性比另一种富勒烯醇低得多，其程度是质谱仅显示出环氧化物。两种C_（60）F_（35）OH异构体均具有C_1对称性，其异构体通过〜（19）F NMR光谱中的化学位移与C_1 C_（60）F_（36）光谱中的化学位移之间显着的线性关系来鉴定;另一个的光谱显示通过用OH取代一个F使C_3 C_（60）F_（36）的图案不对称。分离的双键的存在促进了反应，并提供了富勒烯衍生物的S_N2'反应的第一个证明实例。我们的观察解释了为什么在C_（60）F_（36）中仅容易替换有限数量的氟，以及为什么C_（60）F_（18）相反更耐水解。我们还分离了C_（60）F_（36）O的纯异构体，该异构体显示为显然来自C_1 C_（60）F_（36）的氧杂富勒烯（醚），以及不纯的馏分，其中包含C_（60）F_（36），C_（60）F_（36）的三氟甲基衍生物，C_（60）F_（36）O的第二个异构体以及1392 u的未知物种。

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