Preparation of carbamates

Gorodetskii, L. Sh.; Volzhina, O. N.; Кузнецова, И. А.; Alekseeva, E. N.

doi:10.1007/bf00759756

Cited by 1 publication

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“…From this point of view, a new practical and highly selective aziridination of C 60 with alternative nitrogen sources instead of azides and generally applicable isomerization of an aziridinofullerene to an azafulleroid are desired. Here we report a new type of selective aziridination of C 60 with a variety of simple amides, many of which are either commercially available or readily prepared from either corresponding acids, alcohols, or amines . Moreover, catalytic rearrangement of the resulting aziridinofullerenes to azafulleroids with use of a chloramine salt and an MS4A system was investigated.…”

Section: Introductionmentioning

confidence: 99%

Aziridination of C₆₀ with Simple Amides and Catalytic Rearrangement of the Aziridinofullerenes to Azafulleroids

et al. 2009

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The selective formation of aziridinofullerene and azafulleroid, which are isomers of the fullerene derivatives-introduced N(1) unit, is achieved. The ionic aziridination is a very convenient and risk-free procedure compared with the conventional method with azides as nitrogen sources, and gives aziridinofullerenes from various readily available amides (carbamates, ureas, carboxamides, and phosphamides). For example, benzyl carbamate was chlorinated by tert-butyl hypochlorite (tert-BuOCl) and then reacted with C(60) in the presence of base to give N-benzyloxycarbonyl aziridinofullerene exclusively and without formation of its isomer, an azafulleroid. The reaction enabled the synthesis of functional fullerene derivatives having a trialkoxysilyl group and an amino acid moiety. Azafulleroids were obtained through the rearrangement of corresponding aziridinofullerenes by using the combination of a chloramine catalyst and MS4A. Among other chloramines used, chloramine B (CB) showed superior ability as a catalyst in the rearrangement. It was found that MS4A functions as a Lewis acid in the reaction.

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Section: Introductionmentioning

confidence: 99%

Aziridination of C₆₀ with Simple Amides and Catalytic Rearrangement of the Aziridinofullerenes to Azafulleroids

et al. 2009

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show abstract

Preparation of carbamates

Cited by 1 publication

References 8 publications

Aziridination of C₆₀ with Simple Amides and Catalytic Rearrangement of the Aziridinofullerenes to Azafulleroids

Aziridination of C₆₀ with Simple Amides and Catalytic Rearrangement of the Aziridinofullerenes to Azafulleroids

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Preparation of carbamates

Cited by 1 publication

References 8 publications

Aziridination of C60 with Simple Amides and Catalytic Rearrangement of the Aziridinofullerenes to Azafulleroids

Aziridination of C60 with Simple Amides and Catalytic Rearrangement of the Aziridinofullerenes to Azafulleroids

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Aziridination of C₆₀ with Simple Amides and Catalytic Rearrangement of the Aziridinofullerenes to Azafulleroids

Aziridination of C₆₀ with Simple Amides and Catalytic Rearrangement of the Aziridinofullerenes to Azafulleroids