(2,2′)(2,2′)Biphenylophanetriyne: A Twisted Biphenylophane with a Highly Distorted Diacetylene Bridge

Shunpei Nobusue; Hiroshi Yamane; Hirokazu Miyoshi; Tobe Yoshito

doi:10.1021/ol5004934

(2,2′)(2,2′)Biphenylophanetriyne: A Twisted Biphenylophane with a Highly Distorted Diacetylene Bridge

Shunpei Nobusue, Hiroshi Yamane, Hirokazu Miyoshi, Tobe Yoshito^*

^*Corresponding author for this work

Department of Applied Chemistry

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

26 Scopus citations

Abstract

Biphenylophane 1 bridged by acetylene and diacetylene linkages was synthesized. X-ray analysis revealed its highly deformed diacetylene unit with a bond angle of 160°. Enantiomers of 1 resolved by chiral HPLC underwent facile racemization with an activation energy of 90.6 kJ mol^-1. Transannular cyclization of 1 was induced by heating to generate benzyne intermediate 8, which was intercepted by furan to give 9, and by treatment with bromine to give dibromodibenzopicene (10).

Original language	English
Pages (from-to)	1940-1943
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	7
DOIs	https://doi.org/10.1021/ol5004934
State	Published - 4 Apr 2014

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abstract = "Biphenylophane 1 bridged by acetylene and diacetylene linkages was synthesized. X-ray analysis revealed its highly deformed diacetylene unit with a bond angle of 160°. Enantiomers of 1 resolved by chiral HPLC underwent facile racemization with an activation energy of 90.6 kJ mol-1. Transannular cyclization of 1 was induced by heating to generate benzyne intermediate 8, which was intercepted by furan to give 9, and by treatment with bromine to give dibromodibenzopicene (10).",

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AU - Nobusue, Shunpei

AU - Yamane, Hiroshi

AU - Miyoshi, Hirokazu

AU - Yoshito, Tobe

PY - 2014/4/4

Y1 - 2014/4/4

N2 - Biphenylophane 1 bridged by acetylene and diacetylene linkages was synthesized. X-ray analysis revealed its highly deformed diacetylene unit with a bond angle of 160°. Enantiomers of 1 resolved by chiral HPLC underwent facile racemization with an activation energy of 90.6 kJ mol-1. Transannular cyclization of 1 was induced by heating to generate benzyne intermediate 8, which was intercepted by furan to give 9, and by treatment with bromine to give dibromodibenzopicene (10).

AB - Biphenylophane 1 bridged by acetylene and diacetylene linkages was synthesized. X-ray analysis revealed its highly deformed diacetylene unit with a bond angle of 160°. Enantiomers of 1 resolved by chiral HPLC underwent facile racemization with an activation energy of 90.6 kJ mol-1. Transannular cyclization of 1 was induced by heating to generate benzyne intermediate 8, which was intercepted by furan to give 9, and by treatment with bromine to give dibromodibenzopicene (10).

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U2 - 10.1021/ol5004934

DO - 10.1021/ol5004934

M3 - Article

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VL - 16

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JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

(2,2′)(2,2′)Biphenylophanetriyne: A Twisted Biphenylophane with a Highly Distorted Diacetylene Bridge

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