Generation and Trapping of Ketenes in Flow

Autor:	Cyril Henry, Helen F. Sneddon, David C. Harrowven, Xunli Zhang, Bogdan Ibanescu, Sally Bloodworth, Andy Craven, Richard J. Whitby, David Bolien
Rok vydání:	2015
Předmět:	Tertiary amine 010405 organic chemistry Organic Chemistry Thermal decomposition Kinetics Ketene Infrared spectroscopy Flow chemistry 010402 general chemistry Photochemistry 01 natural sciences 0104 chemical sciences Catalysis Acylation chemistry.chemical_compound chemistry Organic chemistry Physical and Theoretical Chemistry
Zdroj:	European Journal of Organic Chemistry. 2015:1491-1499
ISSN:	1434-193X
DOI:	10.1002/ejoc.201403603
Popis:	Ketenes were generated by the thermolysis of alkoxyalkynes under flow conditions, and then trapped with amines and alcohols to cleanly give amides and esters. For a 10 min reaction time, temperatures of 180, 160, and 140 °C were required for >95 % conversion of EtO, iPrO, and tBuO alkoxyalkynes, respectively. Variation of the temperature and flow rate with inline monitoring of the output by IR spectroscopy allowed the kinetic parameters for the conversion of 1-ethoxy-1-octyne to be easily estimated (Ea = 105.4 kJ/mol). Trapping of the in-situ-generated ketenes by alcohols to give esters required the addition of a tertiary amine catalyst to prevent competitive [2+2] addition of the ketene to the alkoxyalkyne precursor.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::0591e0a91405c14f6c86113812d292b7 https://doi.org/10.1002/ejoc.201403603 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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