Rearrangement of dypnones to 1,3,5-triarylbenzenes

Kai Deng; Qi Yong Huai; Zhi Lun Shen; Hui Jing Li; Chen Liu; Yan Chao Wu

doi:10.1021/acs.orglett.5b00353

Rearrangement of dypnones to 1,3,5-triarylbenzenes

Kai Deng
, Qi Yong Huai
, Zhi Lun Shen
, Hui Jing Li^*
, Chen Liu
, Yan Chao Wu

^*Corresponding author for this work

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

38 Scopus citations

Abstract

Rearrangement of dypnones to 1,3,5-triarylbenzenes is described. The reaction is proposed to involve an aldol-type self-condensation of dypnones, followed by an intramolecular [2 + 2] cycloaddition and a retro-[2 + 2] cycloaddition. The reaction goes smoothly under obviously milder conditions in comparison to the cyclotrimerization of acetophenones to 1,3,5-triarylbenzenes (10 mol % of TsOH, 80 °C versus 130-148 °C). This unexpected rearrangement would provide new possible considerations in dypnone-involved organic synthesis.

Original language	English
Pages (from-to)	1473-1476
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	6
DOIs	https://doi.org/10.1021/acs.orglett.5b00353
State	Published - 20 Mar 2015
Externally published	Yes

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title = "Rearrangement of dypnones to 1,3,5-triarylbenzenes",

abstract = "Rearrangement of dypnones to 1,3,5-triarylbenzenes is described. The reaction is proposed to involve an aldol-type self-condensation of dypnones, followed by an intramolecular [2 + 2] cycloaddition and a retro-[2 + 2] cycloaddition. The reaction goes smoothly under obviously milder conditions in comparison to the cyclotrimerization of acetophenones to 1,3,5-triarylbenzenes (10 mol \% of TsOH, 80 °C versus 130-148 °C). This unexpected rearrangement would provide new possible considerations in dypnone-involved organic synthesis.",

author = "Kai Deng and Huai, \{Qi Yong\} and Shen, \{Zhi Lun\} and Li, \{Hui Jing\} and Chen Liu and Wu, \{Yan Chao\}",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

month = mar,

day = "20",

doi = "10.1021/acs.orglett.5b00353",

language = "英语",

volume = "17",

pages = "1473--1476",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Rearrangement of dypnones to 1,3,5-triarylbenzenes

AU - Deng, Kai

AU - Huai, Qi Yong

AU - Shen, Zhi Lun

AU - Li, Hui Jing

AU - Liu, Chen

AU - Wu, Yan Chao

PY - 2015/3/20

Y1 - 2015/3/20

N2 - Rearrangement of dypnones to 1,3,5-triarylbenzenes is described. The reaction is proposed to involve an aldol-type self-condensation of dypnones, followed by an intramolecular [2 + 2] cycloaddition and a retro-[2 + 2] cycloaddition. The reaction goes smoothly under obviously milder conditions in comparison to the cyclotrimerization of acetophenones to 1,3,5-triarylbenzenes (10 mol % of TsOH, 80 °C versus 130-148 °C). This unexpected rearrangement would provide new possible considerations in dypnone-involved organic synthesis.

AB - Rearrangement of dypnones to 1,3,5-triarylbenzenes is described. The reaction is proposed to involve an aldol-type self-condensation of dypnones, followed by an intramolecular [2 + 2] cycloaddition and a retro-[2 + 2] cycloaddition. The reaction goes smoothly under obviously milder conditions in comparison to the cyclotrimerization of acetophenones to 1,3,5-triarylbenzenes (10 mol % of TsOH, 80 °C versus 130-148 °C). This unexpected rearrangement would provide new possible considerations in dypnone-involved organic synthesis.

UR - https://www.scopus.com/pages/publications/84925370884

U2 - 10.1021/acs.orglett.5b00353

DO - 10.1021/acs.orglett.5b00353

M3 - 文章

AN - SCOPUS:84925370884

SN - 1523-7060

VL - 17

SP - 1473

EP - 1476

JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

Rearrangement of dypnones to 1,3,5-triarylbenzenes

Abstract

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