(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^*

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摘要

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).

原文	English
頁（從 - 到）	1940-1943
頁數	4
期刊	Organic Letters
卷	16
發行號	7
DOIs	https://doi.org/10.1021/ol5004934
出版狀態	Published - 4 4月 2014

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10.1021/ol5004934

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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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T1 - (2,2′)(2,2′)Biphenylophanetriyne

T2 - A Twisted Biphenylophane with a Highly Distorted Diacetylene Bridge

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

AN - SCOPUS:84898751919

SN - 1523-7060

VL - 16

SP - 1940

EP - 1943

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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