Synthesis and structures of [2n](2,7)naphthalenophanes (n = 2-4)

Kenta Ohtsuka; Guangke Cai; Kazuya Fujita; Hirokazu Miyoshi; Yoshito Tobe

doi:10.1139/cjc-2016-0583

Synthesis and structures of [2_n](2,7)naphthalenophanes (n = 2-4)

Kenta Ohtsuka, Guangke Cai, Kazuya Fujita, Hirokazu Miyoshi, Yoshito Tobe^*

^*Corresponding author for this work

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

Reductive coupling of 2,7-bis(bromomethyl)naphthalene using phenyllithium gave anti-[2₂](2,7)naphthalenophane, [2₃](2,7)naphthalenophane, and [2₄](2,7)naphthalenophane, the distribution of which was dependent on the reaction conditions. The structure of the first compound was established by X-ray crystallographic analysis. On the basis of the similarity between the NMR and UV spectra of [2₃](2,7)naphthalenophane with those reported for syn-[2₂](2,7)naphthalenophane, we conclude that the compound originally assigned to be syn-4 was in fact 6.

Original language	English
Pages (from-to)	445-449
Number of pages	5
Journal	Canadian Journal of Chemistry
Volume	95
Issue number	4
DOIs	https://doi.org/10.1139/cjc-2016-0583
State	Published - 1 Jan 2017

Keywords

Aromatic compounds
Cyclophanes
Reductive coupling
X-ray crystal structure analysis

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abstract = "Reductive coupling of 2,7-bis(bromomethyl)naphthalene using phenyllithium gave anti-[22](2,7)naphthalenophane, [23](2,7)naphthalenophane, and [24](2,7)naphthalenophane, the distribution of which was dependent on the reaction conditions. The structure of the first compound was established by X-ray crystallographic analysis. On the basis of the similarity between the NMR and UV spectra of [23](2,7)naphthalenophane with those reported for syn-[22](2,7)naphthalenophane, we conclude that the compound originally assigned to be syn-4 was in fact 6.",

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T1 - Synthesis and structures of [2n](2,7)naphthalenophanes (n = 2-4)

AU - Ohtsuka, Kenta

AU - Cai, Guangke

AU - Fujita, Kazuya

AU - Miyoshi, Hirokazu

AU - Tobe, Yoshito

PY - 2017/1/1

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N2 - Reductive coupling of 2,7-bis(bromomethyl)naphthalene using phenyllithium gave anti-[22](2,7)naphthalenophane, [23](2,7)naphthalenophane, and [24](2,7)naphthalenophane, the distribution of which was dependent on the reaction conditions. The structure of the first compound was established by X-ray crystallographic analysis. On the basis of the similarity between the NMR and UV spectra of [23](2,7)naphthalenophane with those reported for syn-[22](2,7)naphthalenophane, we conclude that the compound originally assigned to be syn-4 was in fact 6.

AB - Reductive coupling of 2,7-bis(bromomethyl)naphthalene using phenyllithium gave anti-[22](2,7)naphthalenophane, [23](2,7)naphthalenophane, and [24](2,7)naphthalenophane, the distribution of which was dependent on the reaction conditions. The structure of the first compound was established by X-ray crystallographic analysis. On the basis of the similarity between the NMR and UV spectra of [23](2,7)naphthalenophane with those reported for syn-[22](2,7)naphthalenophane, we conclude that the compound originally assigned to be syn-4 was in fact 6.

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KW - X-ray crystal structure analysis

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