Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Zeitschrift für Physikalische Chemie

International journal of research in physical chemistry and chemical physics

Editor-in-Chief: Rademann, Klaus


IMPACT FACTOR 2018: 0.975
5-year IMPACT FACTOR: 1.021

CiteScore 2018: 1.20

SCImago Journal Rank (SJR) 2018: 0.327
Source Normalized Impact per Paper (SNIP) 2018: 0.391

Online
ISSN
2196-7156
See all formats and pricing
More options …
Volume 228, Issue 2-3

Issues

Stereoselective Di-pi-Methane Rearrangement of a BINOL-Substituted Dibenzobarrelene Derivative

Heiko Ihmels
  • Corresponding author
  • Universität Siegen, Department Chemie-Biologie, Adolf-Reichwein-Str. 2, 57068 Siegen, Germany
  • Email
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Jia Luo
  • Universität Siegen, Department Chemie-Biologie, Adolf-Reichwein-Str. 2, 57068 Siegen, Germany
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2014-02-07 | DOI: https://doi.org/10.1515/zpch-2014-0462

Abstract

Two dibenzobarrelene derivatives were synthesized that are covalently linked to a (S)-BINOL unit through an oxymethylene (1b) or ethylenedioxymethylene (1c) unit, and their photoreactivity was examined. Irradiation of 1b in acetone resulted in a di-π-methane rearrangement to give diastereoselectively one dibenzosemibullvalene isomer. Experimental and theoretical data point to a directing effect of the BINOL auxiliary based on steric repulsion. The derivative 1c with a longer linker between the BINOL unit and the dibenzobarrelene is photoinert, presumably because of fast competing relaxation processes in the excited state.

Keywords: Photochemistry; Selective Photoreactions

About the article

Accepted: 2013-11-26

Received: 2013-10-04

Published Online: 2014-02-07

Published in Print: 2014-03-28


Citation Information: Zeitschrift für Physikalische Chemie, Volume 228, Issue 2-3, Pages 229–242, ISSN (Online) 2196-7156, ISSN (Print) 0942-9352, DOI: https://doi.org/10.1515/zpch-2014-0462.

Export Citation

©2014 Walter de Gruyter Berlin/Boston.Get Permission

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

[1]
Andreas Tröster and Thorsten Bach
Chemical Communications, 2019

Comments (0)

Please log in or register to comment.
Log in