The profound effect of the ring size in the electrocyclic opening of cyclobutene-fused bicyclic systems

Michael J Robertson-Ralph; David C. Harrowven; Steven Gaulier; Sean Ng; Kevin I. Booker-Milburn

doi:10.1002/anie.201410115

The profound effect of the ring size in the electrocyclic opening of cyclobutene-fused bicyclic systems

Michael J Robertson-Ralph, David C. Harrowven, Steven Gaulier, Sean Ng, Kevin I. Booker-Milburn^*

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

37 Citations (Scopus)

Abstract

Fused cyclobutenes, prepared by the photocycloaddition of propargyl alcohols to cyclic anhydride chromophores, undergo facile thermochemical ring opening to fused γ-lactones. The size of the fused ring profoundly influences the temperature that is required to facilitate the ring opening (from 50°C to 180°C) and the nature of the product that is formed. Our studies provide new insights into the mechanistic course of these reactions and have been extended to facilitate the preparation of lactams fused to medium-sized rings.

Original language	English
Pages (from-to)	1527-1531
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	5
DOIs	https://doi.org/10.1002/anie.201410115
Publication status	Published - 26 Jan 2015

Research Groups and Themes

BCS and TECS CDTs

Keywords

Cyclobutenes
Electrocyclic reactions
Fused-ring systems
Photochemistry
Ring opening

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10.1002/anie.201410115

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Cite this

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title = "The profound effect of the ring size in the electrocyclic opening of cyclobutene-fused bicyclic systems",

abstract = "Fused cyclobutenes, prepared by the photocycloaddition of propargyl alcohols to cyclic anhydride chromophores, undergo facile thermochemical ring opening to fused γ-lactones. The size of the fused ring profoundly influences the temperature that is required to facilitate the ring opening (from 50°C to 180°C) and the nature of the product that is formed. Our studies provide new insights into the mechanistic course of these reactions and have been extended to facilitate the preparation of lactams fused to medium-sized rings.",

keywords = "Cyclobutenes, Electrocyclic reactions, Fused-ring systems, Photochemistry, Ring opening",

author = "Robertson-Ralph, {Michael J} and Harrowven, {David C.} and Steven Gaulier and Sean Ng and Booker-Milburn, {Kevin I.}",

year = "2015",

month = jan,

day = "26",

doi = "10.1002/anie.201410115",

language = "English",

volume = "54",

pages = "1527--1531",

journal = "Angewandte Chemie - International Edition",

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T1 - The profound effect of the ring size in the electrocyclic opening of cyclobutene-fused bicyclic systems

AU - Robertson-Ralph, Michael J

AU - Harrowven, David C.

AU - Gaulier, Steven

AU - Ng, Sean

AU - Booker-Milburn, Kevin I.

PY - 2015/1/26

Y1 - 2015/1/26

N2 - Fused cyclobutenes, prepared by the photocycloaddition of propargyl alcohols to cyclic anhydride chromophores, undergo facile thermochemical ring opening to fused γ-lactones. The size of the fused ring profoundly influences the temperature that is required to facilitate the ring opening (from 50°C to 180°C) and the nature of the product that is formed. Our studies provide new insights into the mechanistic course of these reactions and have been extended to facilitate the preparation of lactams fused to medium-sized rings.

AB - Fused cyclobutenes, prepared by the photocycloaddition of propargyl alcohols to cyclic anhydride chromophores, undergo facile thermochemical ring opening to fused γ-lactones. The size of the fused ring profoundly influences the temperature that is required to facilitate the ring opening (from 50°C to 180°C) and the nature of the product that is formed. Our studies provide new insights into the mechanistic course of these reactions and have been extended to facilitate the preparation of lactams fused to medium-sized rings.

KW - Cyclobutenes

KW - Electrocyclic reactions

KW - Fused-ring systems

KW - Photochemistry

KW - Ring opening

UR - http://www.scopus.com/inward/record.url?scp=84920059320&partnerID=8YFLogxK

U2 - 10.1002/anie.201410115

DO - 10.1002/anie.201410115

M3 - Article (Academic Journal)

C2 - 25483597

AN - SCOPUS:84921504698

SN - 1433-7851

VL - 54

SP - 1527

EP - 1531

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 5

ER -

The profound effect of the ring size in the electrocyclic opening of cyclobutene-fused bicyclic systems

Abstract

Research Groups and Themes

Keywords

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3-month Core Capability for Chemistry Research

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The profound effect of the ring size in the electrocyclic opening of cyclobutene-fused bicyclic systems

Abstract

Research Groups and Themes

Keywords

Access to Document

Handle.net

Other files and links

Fingerprint

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3-month Core Capability for Chemistry Research

Cite this