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SET-promoted photoaddition reactions of fullerene C-60 with tertiary N-trimethylsilylmethyl substituted alpha-aminonitriles. Approach to the synthesis of fulleropyrrolidine nitriles

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Title
SET-promoted photoaddition reactions of fullerene C-60 with tertiary N-trimethylsilylmethyl substituted alpha-aminonitriles. Approach to the synthesis of fulleropyrrolidine nitriles
Author(s)
Suk Hyun Lim; Dae Won Cho; Jungkweon Choi; Hyunjun An; Jun Ho Shim; Patrick S. Mariano
Publication Date
2017-11
Journal
TETRAHEDRON, v.73, no.44, pp.6249 - 6261
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Abstract
Photoaddition reactions of C-60 with tertiary N-arylmethyl-N-trimethylsilylmethyl substituted alpha-aminonitriles were explored. The results show that these photoreactions produce both trimethylsilyl- and cyano group containing fulleropyrrolidines as major products through pathways involving 1,3-dipolar cycloaddition of azomethine ylide intermediates. The ylides are formed either by SET from alpha-aminonitriles to the triplet excited state of C-60 (in N-2-purged solutions) followed by desilylation or deprotonation, or by hydrogen atom abstraction by singlet oxygen (in O-2-purged solutions). In contrast, photoreactions of C-60 with analogous amines that do not contain trimethylsilyl group form fulleropyrrolidines that contain aryl- and cyano substitutents on the pyrrolidine ring. The efficiencies of these photoaddition reactions are influenced by several factors including reaction condition (N-2 or O-2-purged), solvent polarity, the electronic and structural nature of alpha-aminonitriles and additive. The presence of trimethylsilyl group in the alpha-aminonitrile substrates plays a crucial role in enhancing the efficiencies of the fulleropyrrolidine forming reactions. (C) 2017 Elsevier Ltd. All rights reserved
URI
https://pr.ibs.re.kr/handle/8788114/4026
ISSN
0040-4020
Appears in Collections:
Center for Nanomaterials and Chemical Reactions(나노물질 및 화학반응 연구단) > Journal Papers (저널논문)
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