[60]富勒烯和醇钠、苯肼、胺的反应研究
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摘要
在富勒烯化学中,化学修饰一直是富勒烯研究的主要领域之一。至今,大量的功能富勒烯衍生物已经被人们合成出来,它们在材料科学,生命科学等方面都具有潜在的巨大应用价值。新型富勒烯衍生物的合成研究一直都具有重要的意义,而对富勒烯衍生物进行二次衍生化也是制备功能富勒烯衍生物的重要反应。本文主要工作是合成了几类新型的富勒烯衍生物,并对其进行了一系列二次衍生化研究。
1.系统的研究了C_(60)与新鲜配置的醇钠溶液在O_2存在条件下的反应,得到了一系列氧原子直接与C_(60)分子相连的富勒烯四氢呋喃结构的衍生物。这种四氢呋喃环合富勒烯衍生物作为一个合成中间体又可发生进一步的衍生化反应,其与不同当量BF_3·OEt_2在不同温度条件下可以得到二氢呋喃环合富勒烯衍生物、三元环合富勒烯衍生物等。
2.通过C_(60)和取代苯肼盐酸盐,亚硝酸钠在水和O_2存在条件下的反应,合成了单加成的1,4-富勒醇,成功分离和鉴定了反应的重要中间体C_(60)Ar(NO_2),并对机理进行了系列研究,提出了一种可能通过S_N2'途径的机理。在对甲苯磺酸的作用下我们还对1,4-富勒醇进行了一系列再衍生化研究,成功实现了酯化,醚化和芳基化反应。
3.通过一级胺在醋酸碘苯氧化下形成氮宾,再在醋酸铜促进下发生转移,与C_(60)发生[2+1]反应,选择性地得到一系列闭环氮撑富勒烯衍生物,提供了一种直接选择性合成闭环氮撑富勒烯衍生物的有效方法。
4.通过PhI(OAc)_2和Cu(OH)Cl-TMEDA催化的C_(60)与一级磺酰胺的反应,得到了一种新型的咪唑啉环合富勒烯衍生物,这是第一次报道这种类型的产物。此外,Cu(OH)Cl·TMEDA和Cu(OAc)_2·H_2O显示出了不同的选择性。
Chemical modification is one of the most important research fields in the fullerene chemistry.Many functionalized fullerene derivatives have been synthesized till now,which have potential applications in material and medicine science.There is great significance in the synthesis of novel fullerene derivatives.While further functionalization of fullerene derivatives is one of the important methods to synthesize new functionized fullerene derivatives.In this dissertation,several new types of fuUerene derivatives were synthesized and further functionalization was successfully carried out.
1.The reaction of C_(60) with freshly prepared sodium alkoxide solution under aerobic condition was well investigated,which provides a facile protocol to synthesize a variety of C_(60)-fused tetrahydrofuran derivatives with oxygen atom directly attached to fullerene cage.The C_(60)-fused tetrahydrofuran derivatives are excellent synthons for further functionalization.While treated with different equiv,of BF_3·OEt_2 at various temperature,several novel functionized fullerene derivatives have been successfully synthesized.
2.1,4-Fullerenols C_(60)ArOH were synthesized via the reaction of[60]fullerene with 4-substituted phenylhydrazine hydrochlorides and sodium nitrite under moisture and aerobic conditions.The key and unprecedent intermediate C_(60)Ar(NO_2) was isolated and characterized.A possible mechanism for the formation of 1,4-fullerenols involving C_(60)Ar(NO_2) via a S_N2' pathway was proposed.Further transformations of the 1,4-fullerenols through esterification,etherization,and arylation were also carried out in the presence of p-toluene sulfonic acid.
3.Several primary amines are oxidized by PhI(OAc)_2 to generate nitrenes.Then via copper acetate-promoted transfer,they are selectively added to C_(60) by[2+1] pathway to produce a series of 1,2-aziridino-[60]fullerenes.This is a facile and efficient protocol to synthsize closed 1,2-azabridged aziridinofullerene.
4.By PhI(OAc)_2 and Cu(OH)Cl·TMEDA catalyzed reaction of C_(60) with primary sulonic amins,a new type of C_(60)-fused imidazole derivatives is successfully synthesized.It is the first time to report such fullerene derivatives.
1.系统的研究了C_(60)与新鲜配置的醇钠溶液在O_2存在条件下的反应,得到了一系列氧原子直接与C_(60)分子相连的富勒烯四氢呋喃结构的衍生物。这种四氢呋喃环合富勒烯衍生物作为一个合成中间体又可发生进一步的衍生化反应,其与不同当量BF_3·OEt_2在不同温度条件下可以得到二氢呋喃环合富勒烯衍生物、三元环合富勒烯衍生物等。
2.通过C_(60)和取代苯肼盐酸盐,亚硝酸钠在水和O_2存在条件下的反应,合成了单加成的1,4-富勒醇,成功分离和鉴定了反应的重要中间体C_(60)Ar(NO_2),并对机理进行了系列研究,提出了一种可能通过S_N2'途径的机理。在对甲苯磺酸的作用下我们还对1,4-富勒醇进行了一系列再衍生化研究,成功实现了酯化,醚化和芳基化反应。
3.通过一级胺在醋酸碘苯氧化下形成氮宾,再在醋酸铜促进下发生转移,与C_(60)发生[2+1]反应,选择性地得到一系列闭环氮撑富勒烯衍生物,提供了一种直接选择性合成闭环氮撑富勒烯衍生物的有效方法。
4.通过PhI(OAc)_2和Cu(OH)Cl-TMEDA催化的C_(60)与一级磺酰胺的反应,得到了一种新型的咪唑啉环合富勒烯衍生物,这是第一次报道这种类型的产物。此外,Cu(OH)Cl·TMEDA和Cu(OAc)_2·H_2O显示出了不同的选择性。
Chemical modification is one of the most important research fields in the fullerene chemistry.Many functionalized fullerene derivatives have been synthesized till now,which have potential applications in material and medicine science.There is great significance in the synthesis of novel fullerene derivatives.While further functionalization of fullerene derivatives is one of the important methods to synthesize new functionized fullerene derivatives.In this dissertation,several new types of fuUerene derivatives were synthesized and further functionalization was successfully carried out.
1.The reaction of C_(60) with freshly prepared sodium alkoxide solution under aerobic condition was well investigated,which provides a facile protocol to synthesize a variety of C_(60)-fused tetrahydrofuran derivatives with oxygen atom directly attached to fullerene cage.The C_(60)-fused tetrahydrofuran derivatives are excellent synthons for further functionalization.While treated with different equiv,of BF_3·OEt_2 at various temperature,several novel functionized fullerene derivatives have been successfully synthesized.
2.1,4-Fullerenols C_(60)ArOH were synthesized via the reaction of[60]fullerene with 4-substituted phenylhydrazine hydrochlorides and sodium nitrite under moisture and aerobic conditions.The key and unprecedent intermediate C_(60)Ar(NO_2) was isolated and characterized.A possible mechanism for the formation of 1,4-fullerenols involving C_(60)Ar(NO_2) via a S_N2' pathway was proposed.Further transformations of the 1,4-fullerenols through esterification,etherization,and arylation were also carried out in the presence of p-toluene sulfonic acid.
3.Several primary amines are oxidized by PhI(OAc)_2 to generate nitrenes.Then via copper acetate-promoted transfer,they are selectively added to C_(60) by[2+1] pathway to produce a series of 1,2-aziridino-[60]fullerenes.This is a facile and efficient protocol to synthsize closed 1,2-azabridged aziridinofullerene.
4.By PhI(OAc)_2 and Cu(OH)Cl·TMEDA catalyzed reaction of C_(60) with primary sulonic amins,a new type of C_(60)-fused imidazole derivatives is successfully synthesized.It is the first time to report such fullerene derivatives.
引文
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