Acceleration of Acid-Catalyzed Hydrolysis in a Biphasic System by Sodium Tetracyanocyclopentadienides
The hydrolysis of tert-butyldimethylsilyl L-menthyl ether (3) in a CH2Cl2–1 M HCl biphasic solvent system was accelerated by the addition of sodium tetracyanocyclopentadienides 1. Particularly, the reaction rate was enhanced using sodium salt 1a–c with a lipophilic substituent on the cyclopentadieni...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2016/07/01, Vol.64(7), pp.930-934 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | Sakai, Takeo Bito, Mariko Itakura, Makoto Sato, Honami Mori, Yuji |
| description | The hydrolysis of tert-butyldimethylsilyl L-menthyl ether (3) in a CH2Cl2–1 M HCl biphasic solvent system was accelerated by the addition of sodium tetracyanocyclopentadienides 1. Particularly, the reaction rate was enhanced using sodium salt 1a–c with a lipophilic substituent on the cyclopentadienide ring. From the results obtained by a triphasic experiment, hydrolysis proceeds via the formation of hydronium ion 2 in the aqueous phase by ion exchange, followed by the transfer of 2 to the CH2Cl2 phase. |
| doi_str_mv | 10.1248/cpb.c16-00150 |
| format | Article |
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Particularly, the reaction rate was enhanced using sodium salt 1a–c with a lipophilic substituent on the cyclopentadienide ring. 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From the results obtained by a triphasic experiment, hydrolysis proceeds via the formation of hydronium ion 2 in the aqueous phase by ion exchange, followed by the transfer of 2 to the CH2Cl2 phase.</description><subject>acid-catalyzed reaction</subject><subject>Catalysis</subject><subject>Cyclopentanes - chemistry</subject><subject>Hydrochloric Acid - chemistry</subject><subject>Hydrolysis</subject><subject>Methylene Chloride - chemistry</subject><subject>Molecular Structure</subject><subject>Organosilicon Compounds - chemistry</subject><subject>phase-transfer reaction</subject><subject>Solvents - chemistry</subject><subject>tetracyanocyclopentadienide</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkEFv1DAQhS0EokvhyBVZ4sIlZRw7dnJcVtAiVeLQcrYcZ8J6ldjBzh7Cr8e7KVuJg8eH-fTmvUfIewY3rBT1Zzu1N5bJAoBV8IJsGBeqqMqSvyQbAGiKkkt-Rd6kdAAoK1D8NbkqFVdcinpDcGstDhjN7IKnoadb67piZ2YzLH-wo3dLF8OwJJeo89TQL27am-QsfVjSjCNtF_oQOncc6SPO0djF-GAXO4QJ_Ww6h951mN6SV70ZEr57-q_Jz29fH3d3xf2P2--77X1hparngiHv20bmWLKrchww0DIhVIVNxawAUytroFe2UV2fyR5lw2QjWE7DmWj5Nfm06k4x_D5imvXoUs43GI_hmDSrgdWSiVpk9ON_6CEco8_uVqqs65plqlgpG0NKEXs9RTeauGgG-tS_zv3r3L8-95_5D0-qx3bE7kL_KzwDtyuQt86aIfjBeXy-bZOyexydLuEsKgUoDTy_hsNpiDJnZiCz0m5VOqTZ_MLLKRNnZwc8G5NCq9O4GHze7k3U6PlfVT6usw</recordid><startdate>2016</startdate><enddate>2016</enddate><creator>Sakai, Takeo</creator><creator>Bito, Mariko</creator><creator>Itakura, Makoto</creator><creator>Sato, Honami</creator><creator>Mori, Yuji</creator><general>The Pharmaceutical Society of Japan</general><general>Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>2016</creationdate><title>Acceleration of Acid-Catalyzed Hydrolysis in a Biphasic System by Sodium Tetracyanocyclopentadienides</title><author>Sakai, Takeo ; Bito, Mariko ; Itakura, Makoto ; Sato, Honami ; Mori, Yuji</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c678t-1e3fb962486d51500a0b14475e951c40a87ca0f7c97dffb9fe6916941373314b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>acid-catalyzed reaction</topic><topic>Catalysis</topic><topic>Cyclopentanes - chemistry</topic><topic>Hydrochloric Acid - chemistry</topic><topic>Hydrolysis</topic><topic>Methylene Chloride - chemistry</topic><topic>Molecular Structure</topic><topic>Organosilicon Compounds - chemistry</topic><topic>phase-transfer reaction</topic><topic>Solvents - chemistry</topic><topic>tetracyanocyclopentadienide</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sakai, Takeo</creatorcontrib><creatorcontrib>Bito, Mariko</creatorcontrib><creatorcontrib>Itakura, Makoto</creatorcontrib><creatorcontrib>Sato, Honami</creatorcontrib><creatorcontrib>Mori, Yuji</creatorcontrib><creatorcontrib>Meijo University</creatorcontrib><creatorcontrib>Faculty of Pharmacy</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sakai, Takeo</au><au>Bito, Mariko</au><au>Itakura, Makoto</au><au>Sato, Honami</au><au>Mori, Yuji</au><aucorp>Meijo University</aucorp><aucorp>Faculty of Pharmacy</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Acceleration of Acid-Catalyzed Hydrolysis in a Biphasic System by Sodium Tetracyanocyclopentadienides</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2016</date><risdate>2016</risdate><volume>64</volume><issue>7</issue><spage>930</spage><epage>934</epage><pages>930-934</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>The hydrolysis of tert-butyldimethylsilyl L-menthyl ether (3) in a CH2Cl2–1 M HCl biphasic solvent system was accelerated by the addition of sodium tetracyanocyclopentadienides 1. Particularly, the reaction rate was enhanced using sodium salt 1a–c with a lipophilic substituent on the cyclopentadienide ring. From the results obtained by a triphasic experiment, hydrolysis proceeds via the formation of hydronium ion 2 in the aqueous phase by ion exchange, followed by the transfer of 2 to the CH2Cl2 phase.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>27373648</pmid><doi>10.1248/cpb.c16-00150</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | acid-catalyzed reaction Catalysis Cyclopentanes - chemistry Hydrochloric Acid - chemistry Hydrolysis Methylene Chloride - chemistry Molecular Structure Organosilicon Compounds - chemistry phase-transfer reaction Solvents - chemistry tetracyanocyclopentadienide |
| title | Acceleration of Acid-Catalyzed Hydrolysis in a Biphasic System by Sodium Tetracyanocyclopentadienides |
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