Literature DB >> 34586823

Biphenyl Cyclobutenone Photoelectrocyclizations.

Changhang Dai1, Xuchen Zhao1, Changqing Song1, Zach Schwartz1, Jon D Rainier1.   

Abstract

In this work, we demonstrate that readily available conjugated bis-aryl cyclobutenones undergo photoelectrocyclization reactions to give the corresponding dihydrophenanthrene cyclobutanones when exposed to 350 nm light, TFA, and TMSCl. We have also found that cyclobutenone electrocyclizations and cycloreversions are in equilibrium.

Entities:  

Mesh:

Substances:

Year:  2021        PMID: 34586823      PMCID: PMC8794574          DOI: 10.1021/acs.joc.1c01809

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  15 in total

1.  Unexpected stereodynamic consequences of the restricted rotations in ortho-acyl- and ortho-vinyl biphenyls.

Authors:  Lodovico Lunazzi; Andrea Mazzanti; Mirko Minzoni
Journal:  J Org Chem       Date:  2006-12-08       Impact factor: 4.354

2.  Acetonitrile Activation: An Effective Two-Carbon Unit for Cyclization.

Authors:  Qixue Qin; Xiao Luo; Jialiang Wei; Yuchao Zhu; Xiaojin Wen; Song Song; Ning Jiao
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-18       Impact factor: 15.336

3.  Stereospecific cis- and trans-ring fusions arising from common intermediates.

Authors:  Steven D Townsend; Audrey G Ross; Kai Liu; Samuel J Danishefsky
Journal:  Proc Natl Acad Sci U S A       Date:  2014-05-19       Impact factor: 11.205

4.  Direct Dehydrogenative Arylation of Benzaldehydes with Arenes Using Transient Directing Groups.

Authors:  Da-Yu Wang; Shi-Huan Guo; Gao-Fei Pan; Xue-Qing Zhu; Ya-Ru Gao; Yong-Qiang Wang
Journal:  Org Lett       Date:  2018-03-09       Impact factor: 6.005

5.  Direct and Catalytic Amide Synthesis from Ketones via Transoximation and Beckmann Rearrangement under Mild Conditions.

Authors:  Kengo Hyodo; Genna Hasegawa; Naoki Oishi; Kazuma Kuroda; Kingo Uchida
Journal:  J Org Chem       Date:  2018-10-24       Impact factor: 4.354

Review 6.  Cyclobutenones and Benzocyclobutenones: Versatile Synthons in Organic Synthesis.

Authors:  Peng-Hao Chen; Guangbin Dong
Journal:  Chemistry       Date:  2016-09-13       Impact factor: 5.236

7.  Cross dehydrogenative coupling via base-promoted homolytic aromatic substitution (BHAS): synthesis of fluorenones and xanthones.

Authors:  Sebastian Wertz; Dirk Leifert; Armido Studer
Journal:  Org Lett       Date:  2013-02-01       Impact factor: 6.005

8.  Photoelectrocyclization Reactions of Conjugated Cycloalkenones: Scope and Reactivity.

Authors:  Xuchen Zhao; Changqing Song; Jon D Rainier
Journal:  J Org Chem       Date:  2020-04-01       Impact factor: 4.354

9.  Stereodivergent Photoelectrocyclization Reactions of Bis-aryl Cycloalkenones: Intercepting Photoelectrocyclization Intermediates with Acid.

Authors:  Xuchen Zhao; Changqing Song; Jon D Rainier
Journal:  Org Lett       Date:  2019-10-17       Impact factor: 6.005

10.  The Synthesis of Conjugated Bis-Aryl Vinyl Substrates and Their Photoelectrocyclization Reactions towards Phenanthrene Derivatives.

Authors:  Xuchen Zhao; Jon D Rainier
Journal:  Synthesis (Stuttg)       Date:  2021-01-11       Impact factor: 3.157

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.