Journal of Organic Chemistry Research

Modern Organic Chemistry Research

10.22606/mocr ◽

2020 ◽

Keyword(s):

Organic Chemistry ◽

Chemistry Research

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Scope of the reductive aldol reaction: application to aromatic carbocycles and heterocyclesThis is one of a number of contributions from the current members of the Dyson Perrins Laboratory to mark the end of almost 90 years of organic chemistry research in that building, as all its current academic staff move across South Parks Road to a new purpose-built laboratory.

Organic & Biomolecular Chemistry ◽

10.1039/b306937k ◽

2003 ◽

Vol 1 (21) ◽

pp. 3749 ◽

Cited By ~ 26

Author(s):

Timothy J. Donohoe ◽

David House ◽

K. W. Ace

Keyword(s):

Organic Chemistry ◽

Academic Staff ◽

Aldol Reaction ◽

Chemistry Research ◽

Reductive Aldol

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Reflections on spontaneous asymmetric synthesis by amplifying autocatalysisThis is one of a number of contributions from the current members of the Dyson Perrins Laboratory to mark the end of almost 90 years of organic chemistry research in that building, as all its current academic staff move across South Parks Road to a new purpose-built laboratory.

Organic & Biomolecular Chemistry ◽

10.1039/b307382n ◽

2003 ◽

Vol 1 (21) ◽

pp. 3811 ◽

Cited By ~ 90

Author(s):

Ilya D. Gridnev ◽

Joerg M. Serafimov ◽

Harry Quiney ◽

John M. Brown

Keyword(s):

Organic Chemistry ◽

Asymmetric Synthesis ◽

Academic Staff ◽

Chemistry Research

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Emil Fischer—Unequalled Classicist, Master of Organic Chemistry Research, and Inspired Trailblazer of Biological Chemistry

Angewandte Chemie International Edition ◽

10.1002/anie.200390093 ◽

2003 ◽

Vol 42 (3) ◽

pp. 252-252 ◽

Cited By ~ 2

Author(s):

Horst Kunz

Keyword(s):

Organic Chemistry ◽

Biological Chemistry ◽

Chemistry Research

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Ring Contraction Reactions of a Non-Benzenoid Aromatic Cation and a Neutral Homoaromatic System into Benzene Derivatives

10.26434/chemrxiv-2021-lrkb9-v2 ◽

2021 ◽

Author(s):

Demelza Lyons ◽

An Huy Dinh ◽

Nhan Nu Hong Ton ◽

Reece Crocker ◽

Binh Khanh Mai ◽

...

Keyword(s):

Organic Chemistry ◽

Benzene Ring ◽

Benzene Derivatives ◽

Ring Contraction ◽

Chemistry Research ◽

Synthetic Utility ◽

Aromatic Ions ◽

Benzyl Halides ◽

Tropylium Salts ◽

Ring Contraction Reaction

Aromaticity is one of the most intriguing concepts in organic chemistry. Simple and extended benzenoid aromatic systems have been very well established in undergraduate textbooks, and there are also mentions of non-benzenoid aromatic structures such as cyclopropenium, cyclopentadienide and cycloheptatrienylium (tropylium) ions. However, the structural relationship and the comparison of stabilization energy of such aromatic ions to benzene ring have been rarely studied and remained an underexplored area of advanced organic chemistry research. To contribute some insights into this topic, we focused on the chemical transformation, namely a ring contraction reaction, of the tropylium ion to benzene ring in this work. With an approach combining computational studies with experimental reactions, we also aim to turn this transformation into a synthetically useful tool. Indeed, this work led to the development of a new synthetic protocol, which involved an oxidative ring-contraction of tropylium ion, to formally introduce the phenyl ring onto a range of organic structures. Furthermore, the homoaromatic cycloheptatrienyl precursors of tropylium salts used in these reactions can also be rearranged to valuable benzhydryl or benzyl halides, enriching the synthetic utility of this ring-contraction protocol.

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