The addition of nitrile oxides to [60]fullerene, leading to isoxazolinofullerenes, can be reversed using reducing agents such as Mo(CO)6 or DIBALH. Thus, this reaction can be used, in principle, for protection/deprotection of [60]fullerene or for solubilization purposes. The tether-controlled tandem addition of nitrile oxides and azomethine ylides provides mainly cis-1 patterns. The determination of the structure of bisadducts was obtained by NMR spectroscopy with the help of HMQC, HMBC, and NOEDS techniques. The isoxazoline moiety could be removed using Mo(CO)6 leaving a fulleropyrrolidine derivative
Additions of Azomethine Ylides to Fullerene C60 Assisted by a Removable Anchor / DA ROS, Tatiana; Prato, Maurizio; V., Lucchini. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 65:(2000), pp. 4289-4297.
Additions of Azomethine Ylides to Fullerene C60 Assisted by a Removable Anchor
DA ROS, TATIANA;PRATO, MAURIZIO;
2000-01-01
Abstract
The addition of nitrile oxides to [60]fullerene, leading to isoxazolinofullerenes, can be reversed using reducing agents such as Mo(CO)6 or DIBALH. Thus, this reaction can be used, in principle, for protection/deprotection of [60]fullerene or for solubilization purposes. The tether-controlled tandem addition of nitrile oxides and azomethine ylides provides mainly cis-1 patterns. The determination of the structure of bisadducts was obtained by NMR spectroscopy with the help of HMQC, HMBC, and NOEDS techniques. The isoxazoline moiety could be removed using Mo(CO)6 leaving a fulleropyrrolidine derivativePubblicazioni consigliate
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