Synthesis 2017; 49(03): 539-553
DOI: 10.1055/s-0036-1588645
feature
© Georg Thieme Verlag Stuttgart · New York

Photocaged Hydrocarbons, Aldehydes, Ketones, Enones, and Carboxylic Acids and Esters that Release by the Norrish II Cleavage Protocol and Beyond: Controlled Photoinduced Fragrance Release

Autoren

  • Axel G. Griesbeck*

    a   Department of Chemistry, University of Cologne, Greinstr. 4, 50939 Köln, Germany   eMail: griesbeck@uni-koeln.de
  • Björn Porschen

    a   Department of Chemistry, University of Cologne, Greinstr. 4, 50939 Köln, Germany   eMail: griesbeck@uni-koeln.de
  • Christian Kropf*

    b   Henkel AG & Co. KgaA, Henkelstr. 67, 40589 Düsseldorf, Germany
  • Agnieszka Landes

    a   Department of Chemistry, University of Cologne, Greinstr. 4, 50939 Köln, Germany   eMail: griesbeck@uni-koeln.de
  • Olga Hinze

    a   Department of Chemistry, University of Cologne, Greinstr. 4, 50939 Köln, Germany   eMail: griesbeck@uni-koeln.de
  • Ursula Huchel

    b   Henkel AG & Co. KgaA, Henkelstr. 67, 40589 Düsseldorf, Germany
  • Thomas Gerke

    b   Henkel AG & Co. KgaA, Henkelstr. 67, 40589 Düsseldorf, Germany
Weitere Informationen

Publikationsverlauf

Received: 13. Oktober 2016

Accepted after revision: 13. Oktober 2016

Publikationsdatum:
01. Dezember 2016 (online)


Graphical Abstract

Abstract

Five families of caged fragrance compounds that allow the storage and release of the following small volatile organic molecules are described: terpene hydrocarbons, aldehydes, ketones, Michael-type α,β-unsaturated enones, and carboxylic acids and esters. These caged molecules are released by photoexcitation via carbonyl-directed hydrogen-transfer processes and subsequent C–C bond cleavage (Norrish Type II) or by didenitrogenation of diazirines.

Supporting Information