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Choi, Jung Kweon
나노물질 및 화학반응 연구단
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Control of Chemoselectivity of SET-Promoted Photoaddition Reactions of Fullerene C-60 with alpha-Trimethylsilyl Group-Containing N-Alkylglycinates Yielding Aminomethyl-1,2-dihydrofullerenes or Fulleropyrrolidines

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Title
Control of Chemoselectivity of SET-Promoted Photoaddition Reactions of Fullerene C-60 with alpha-Trimethylsilyl Group-Containing N-Alkylglycinates Yielding Aminomethyl-1,2-dihydrofullerenes or Fulleropyrrolidines
Author(s)
Lim, SH; Ahn, M; Wee, KR; Shim, JH; Jungkweon Choi; Doo-Sik Ahn; Cho, DW
Publication Date
2020-10
Journal
Journal of Organic Chemistry, v.85, no.20, pp.12882 - 12900
Publisher
American Chemical Society
Abstract
Knowledge about factors that govern chemoselectivity is pivotal to the design of reactions that are utilized to produce complex organic substances. In the current study, single-electron transfer (SET)-promoted photoaddition reactions of fullerene C-60 with both trimethylsilyl and various alkyl group-containing glycinates and ethyl N-alkyl-N-((trimethylsilyl)methyl)glycinates were explored to evaluate how the nature of N-alkyl substituents of glycinate substrates and reaction conditions govern the chemoselectivity of reaction pathways followed. The results showed that photoreactions of C-60 with glycinates, performed in deoxygenated conditions, produced aminomethyl-1,2-dihydrofullerenes efficiently through a pathway involving the addition of alpha-amino radical intermediates that are generated by sequential SET-solvent-assisted desilylation of glycinate substrates to C-60. Under oxygenated conditions, photoreactions of glycinate substrates, except N-benzyl-substituted analogues, did not take place efficiently owing to quenching of C-3(60)* by oxygen. Interestingly, N-benzyl-substituted glycinates did react under these conditions to form fulleropyrrolidines through a pathway involving 1,3-dipolar cycloaddition of in situ formed azomethine ylides to C-60. The ylide intermediates were formed by regioselective H-atom transfer from glycinates by singlet oxygen. Furthermore, methylene blue (MB)photosensitized reactions of C-60 with glycinates under oxygenated conditions took place efficiently to produce fulleropyrrolidines independent of the nature of N-alkyl substituents of glycinates
URI
https://pr.ibs.re.kr/handle/8788114/8929
DOI
10.1021/acs.joc.0c01324
ISSN
0022-3263
Appears in Collections:
Center for Nanomaterials and Chemical Reactions(나노물질 및 화학반응 연구단) > 1. Journal Papers (저널논문)
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