Synthesis of unsymmetrical alkyl acetals via addition of primary alcohols to allyl ethers mediated by ruthenium complexes

S. Krompiec , Mateusz Penkala , E Kowalska , Robert Penczek , Piotr Bujak , Witold Danikiewicz , Grzegorz Spólnik , Andrzej Kita , Iwona Grudzka

Abstract

Ru-catalyzed synthesis of mixed alkyl-alkyl acetals via addition of primary alcohols to allyl ethers has been extended to include long-chain and/or functionalized substrates. The catalytic systems for these reactions were generated from RuCl 2(PPh 3) 3 and [RuCl 2(1,5-COD)] x and phosphines [PPh 3 or P(p-chlorophenyl) 3] or SbPh 3. Of particular importance is the almost quantitative elimination of transacetalization. The addition proceeds through allyl complexes, not via isomerization of allyl ethers - subsequent addition of ROH to vinyl ethers. © The Author(s) 2011.

Author S. Krompiec - University of Silesia (UŚ) [University of Silesia in Katowice]
S. Krompiec,,
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, Mateusz Penkala - [University of Silesia in Katowice]
Mateusz Penkala,,
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, E Kowalska - [University of Silesia in Katowice]
E Kowalska,,
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, Robert Penczek - [University of Silesia in Katowice]
Robert Penczek,,
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, Piotr Bujak (FC / CPCT) - [University of Silesia (UŚ)]
Piotr Bujak,,
- Chair Of Polymer Chemistry And Technology
- Uniwersytet Śląski w Katowicach
, Witold Danikiewicz - [Institute of Organic Chemistry of the Polish Academy of Sciences]
Witold Danikiewicz,,
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, Grzegorz Spólnik - [Institute of Organic Chemistry of the Polish Academy of Sciences]
Grzegorz Spólnik,,
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, Andrzej Kita - [University of Silesia in Katowice]
Andrzej Kita,,
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, Iwona Grudzka - [University of Silesia in Katowice]
Iwona Grudzka,,
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Journal seriesMonatshefte für Chemie, ISSN 0026-9247, e-ISSN 1434-4475, (A 25 pkt)
Issue year2011
Vol142
No12
Pages1241-1247
ASJC Classification1600 General Chemistry
DOIDOI:10.1007/s00706-011-0638-8
Languageen angielski
Score (nominal)25
Score sourcejournalList
Publication indicators Scopus Citations = 4; WoS Citations = 4; Scopus SNIP (Source Normalised Impact per Paper): 2011 = 0.756; WoS Impact Factor: 2011 = 1.532 (2) - 2011=1.543 (5)
Citation count*5 (2015-04-20)
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* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.
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