PMID- 35530498
OWN - NLM
STAT- PubMed-not-MEDLINE
LR  - 20220510
IS  - 2046-2069 (Electronic)
IS  - 2046-2069 (Linking)
VI  - 9
IP  - 48
DP  - 2019 Sep 3
TI  - Selective Wacker type oxidation of a macrocyclic diene to the corresponding 
      monounsaturated ketone used as fragrance.
PG  - 27865-27873
LID - 10.1039/c9ra04971a [doi]
AB  - A selective reaction method for the efficient conversion of an isomeric mixture 
      of 1,9-cyclohexadecadiene (1,9-CHDD) to the corresponding monounsaturated 
      cyclohexadec-8-en-1-one (8-CHD) is described. 8-CHD was synthesized via Wacker 
      type oxidation at room temperature using a highly electrophilic in situ formed 
      dicationic palladium species. Isomerisation of the diene and over-oxidation of 
      the substrate could be nearly suppressed by suitable reaction control, which has 
      a positive effect on selectivity. The utilization of molecular oxygen as a green 
      oxidant and environmentally benign iron(iii) salts as co-catalysts was 
      successfully applied. This reaction strategy is promising to overcome the low 
      overall reactivity of internal olefins in Wacker type oxidations. In addition, 
      larger scale experiments showed further potential for industrial application.
CI  - This journal is (c) The Royal Society of Chemistry.
FAU - Brunzel, Tom
AU  - Brunzel T
AUID- ORCID: 0000-0002-9566-2722
AD  - Leibniz Institute for Catalysis at the University of Rostock 
      Albert-Einstein-Strasse 29a 18059 Rostock Germany angela.koeckritz@catalysis.de.
FAU - Heppekausen, Johannes
AU  - Heppekausen J
AD  - Symrise AG Muhlenfeldstrasse 1 37603 Holzminden Germany.
FAU - Panten, Johannes
AU  - Panten J
AD  - Symrise AG Muhlenfeldstrasse 1 37603 Holzminden Germany.
FAU - Kockritz, Angela
AU  - Kockritz A
AD  - Leibniz Institute for Catalysis at the University of Rostock 
      Albert-Einstein-Strasse 29a 18059 Rostock Germany angela.koeckritz@catalysis.de.
LA  - eng
PT  - Journal Article
DEP - 20190904
PL  - England
TA  - RSC Adv
JT  - RSC advances
JID - 101581657
PMC - PMC9070781
COIS- There are no conflicts to declare.
EDAT- 2019/09/04 00:00
MHDA- 2019/09/04 00:01
PMCR- 2019/09/04
CRDT- 2022/05/09 04:23
PHST- 2019/07/01 00:00 [received]
PHST- 2019/08/24 00:00 [accepted]
PHST- 2022/05/09 04:23 [entrez]
PHST- 2019/09/04 00:00 [pubmed]
PHST- 2019/09/04 00:01 [medline]
PHST- 2019/09/04 00:00 [pmc-release]
AID - c9ra04971a [pii]
AID - 10.1039/c9ra04971a [doi]
PST - epublish
SO  - RSC Adv. 2019 Sep 4;9(48):27865-27873. doi: 10.1039/c9ra04971a. eCollection 2019 
      Sep 3.