Photochemical studies on bis-sulfide and -sulfone tethered polyenic derivativesDedicated to Jean-Pierre Desvergne.Electronic supplementary information (ESI) available. CCDC 1535549 (4), 1535551 (5), 1535552 (6), 1535553 (6-O), 1535554 (7-OH) and 1535555 (10). For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7ob00551b

This study focusses on the [2 + 2]-photocycloaddition of a symmetric polyenic system tethered by an aryl bis-sulfide or sulfone platform. Using direct irradiation or photosensitization, no expected ladderane product was isolated. In most cases, only tricyclic products including a single cyclobutane...

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Main Authors Guélen, Simon, Blazejak, Max, Chamoreau, Lise-Marie, Huguet, Arnaud, Derenne, Sylvie, Volatron, François, Mouriès-Mansuy, Virginie, Fensterbank, Louis
Format Journal Article
LanguageEnglish
Published 16.05.2017
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Abstract This study focusses on the [2 + 2]-photocycloaddition of a symmetric polyenic system tethered by an aryl bis-sulfide or sulfone platform. Using direct irradiation or photosensitization, no expected ladderane product was isolated. In most cases, only tricyclic products including a single cyclobutane moiety were formed. Irradiation of bis-acrylic precursors in water with encapsulation by a host (cyclodextrin or cucurbituril) provided a stereoselective access to valuable cyclobutyl adducts. This study focusses on the [2 + 2]-photocycloaddition of a symmetric polyenic system tethered by an aryl bis-sulfide or sulfone platform.
AbstractList This study focusses on the [2 + 2]-photocycloaddition of a symmetric polyenic system tethered by an aryl bis-sulfide or sulfone platform. Using direct irradiation or photosensitization, no expected ladderane product was isolated. In most cases, only tricyclic products including a single cyclobutane moiety were formed. Irradiation of bis-acrylic precursors in water with encapsulation by a host (cyclodextrin or cucurbituril) provided a stereoselective access to valuable cyclobutyl adducts. This study focusses on the [2 + 2]-photocycloaddition of a symmetric polyenic system tethered by an aryl bis-sulfide or sulfone platform.
Author Blazejak, Max
Guélen, Simon
Volatron, François
Derenne, Sylvie
Fensterbank, Louis
Huguet, Arnaud
Chamoreau, Lise-Marie
Mouriès-Mansuy, Virginie
AuthorAffiliation UPMC Univ Paris 06
UMR 7616 Laboratoire de Chimie Théorique
CNRS
UMR 7619 METIS
EPHE
Sorbonne Universités
UMR 8232 Institut Parisien de Chimie Moléculaire
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  publication-title: The Chemistry of Cyclobutanes Parts 1 & 2
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  publication-title: Handbook of Synthetic Photochemistry
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  publication-title: Gaussian 09, Revision A.02
  doi: Frisch Trucks Schlegel Scuseria Robb Cheeseman Scalmani Barone Petersson Nakatsuji Li Caricato Marenich Bloino Janesko Gomperts Mennucci Hratchian Ortiz Izmaylov Sonnenberg Williams-young Ding Lipparini Egidi Goings Peng Petrone Henderson Ranasinghe Zakrzewski Gao Rega Zheng Liang Hada Ehara Toyota Fukuda Hasegawa Ishida Nakajima Honda Kitao Nakai Vreven Throssell Montgomery Jr. Peralta Ogliaro Bearpark Heyd Brothers Kudin Staroverov Keith Kobayashi Normand Raghavachari Rendell Burant Iyengar Tomasi Cossi Millam Klene Adamo Cammi Ochterski Martin Morokuma Farkas Foresman Fox
– issn: 2009
  publication-title: Cubanes, fenestranes, ladderanes, prismanes, staffanes and other oligocyclobutanoids
  doi: Hopf Liebman Perks
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Title Photochemical studies on bis-sulfide and -sulfone tethered polyenic derivativesDedicated to Jean-Pierre Desvergne.Electronic supplementary information (ESI) available. CCDC 1535549 (4), 1535551 (5), 1535552 (6), 1535553 (6-O), 1535554 (7-OH) and 1535555 (10). For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7ob00551b
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