Synthesis 2017; 49(03): 539-553
DOI: 10.1055/s-0036-1588645
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© 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

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
› Author Affiliations
Further Information

Publication History

Received: 13 October 2016

Accepted after revision: 13 October 2016

Publication Date:
01 December 2016 (online)


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

 
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