Alkylation of 5-Substituted Tetrazoles with Various Alcohols in 1,2-Dichloroethane in the Presence of BF3·Et2O
The alkylation of 1 H -tetrazole, 5-methyl-1 H -tetrazole, and 5-phenyl-1 H -tetrazole with primary, secondary, and tertiary alcohols, including benzylic and allylic ones, have been studied in 1,2-dichloroethane in the presence of boron trifluoride–diethyl ether complex. Neither primary nor secondar...
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| Veröffentlicht in: | Russian journal of organic chemistry 2020-07, Vol.56 (7), p.1196-1203 |
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| container_title | Russian journal of organic chemistry |
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| creator | Egorov, S. A. Ishchenko, M. A. Prokopovich, Ya. V. Ivanova, V. I. |
| description | The alkylation of 1
H
-tetrazole, 5-methyl-1
H
-tetrazole, and 5-phenyl-1
H
-tetrazole with primary, secondary, and tertiary alcohols, including benzylic and allylic ones, have been studied in 1,2-dichloroethane in the presence of boron trifluoride–diethyl ether complex. Neither primary nor secondary saturated alcohols alkylated tetrazoles in the given system. Tertiary alcohols such
tert
-butyl alcohol and adamantan-1-ol reacted with unsubstituted and 5-substituted tetrazoles to give 70–85% of the corresponding 2-alkyl-5-R-tetrazoles with high regioselectivity. The alkylation of 1
H
-tetrazole with benzyl alcohol afforded 55% of 2-benzyl-2
H
-tetrazole as the only product. The alkylation of 1
H
-tetrazole with various allylic alcohols led to the formation of mixtures of 2-alkyl-2
H
-tetrazoles with isomeric alkyl substituents. |
| doi_str_mv | 10.1134/S107042802007012X |
| format | Article |
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H
-tetrazole, 5-methyl-1
H
-tetrazole, and 5-phenyl-1
H
-tetrazole with primary, secondary, and tertiary alcohols, including benzylic and allylic ones, have been studied in 1,2-dichloroethane in the presence of boron trifluoride–diethyl ether complex. Neither primary nor secondary saturated alcohols alkylated tetrazoles in the given system. Tertiary alcohols such
tert
-butyl alcohol and adamantan-1-ol reacted with unsubstituted and 5-substituted tetrazoles to give 70–85% of the corresponding 2-alkyl-5-R-tetrazoles with high regioselectivity. The alkylation of 1
H
-tetrazole with benzyl alcohol afforded 55% of 2-benzyl-2
H
-tetrazole as the only product. The alkylation of 1
H
-tetrazole with various allylic alcohols led to the formation of mixtures of 2-alkyl-2
H
-tetrazoles with isomeric alkyl substituents.</description><identifier>ISSN: 1070-4280</identifier><identifier>EISSN: 1608-3393</identifier><identifier>DOI: 10.1134/S107042802007012X</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>Alcohol ; Alkylation ; Benzyl alcohol ; Boron ; Butanol ; Chemistry ; Chemistry and Materials Science ; Dichloroethane ; Diethyl ether ; Organic Chemistry ; Regioselectivity ; Substitutes ; Tetrazoles</subject><ispartof>Russian journal of organic chemistry, 2020-07, Vol.56 (7), p.1196-1203</ispartof><rights>Pleiades Publishing, Ltd. 2020</rights><rights>Pleiades Publishing, Ltd. 2020.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c231X-19043a053dd6ae823d7915b8f98a574d9aa490500c34b07235b5b33b1414723d3</citedby><cites>FETCH-LOGICAL-c231X-19043a053dd6ae823d7915b8f98a574d9aa490500c34b07235b5b33b1414723d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1134/S107042802007012X$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1134/S107042802007012X$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids></links><search><creatorcontrib>Egorov, S. A.</creatorcontrib><creatorcontrib>Ishchenko, M. A.</creatorcontrib><creatorcontrib>Prokopovich, Ya. V.</creatorcontrib><creatorcontrib>Ivanova, V. I.</creatorcontrib><title>Alkylation of 5-Substituted Tetrazoles with Various Alcohols in 1,2-Dichloroethane in the Presence of BF3·Et2O</title><title>Russian journal of organic chemistry</title><addtitle>Russ J Org Chem</addtitle><description>The alkylation of 1
H
-tetrazole, 5-methyl-1
H
-tetrazole, and 5-phenyl-1
H
-tetrazole with primary, secondary, and tertiary alcohols, including benzylic and allylic ones, have been studied in 1,2-dichloroethane in the presence of boron trifluoride–diethyl ether complex. Neither primary nor secondary saturated alcohols alkylated tetrazoles in the given system. Tertiary alcohols such
tert
-butyl alcohol and adamantan-1-ol reacted with unsubstituted and 5-substituted tetrazoles to give 70–85% of the corresponding 2-alkyl-5-R-tetrazoles with high regioselectivity. The alkylation of 1
H
-tetrazole with benzyl alcohol afforded 55% of 2-benzyl-2
H
-tetrazole as the only product. The alkylation of 1
H
-tetrazole with various allylic alcohols led to the formation of mixtures of 2-alkyl-2
H
-tetrazoles with isomeric alkyl substituents.</description><subject>Alcohol</subject><subject>Alkylation</subject><subject>Benzyl alcohol</subject><subject>Boron</subject><subject>Butanol</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Dichloroethane</subject><subject>Diethyl ether</subject><subject>Organic Chemistry</subject><subject>Regioselectivity</subject><subject>Substitutes</subject><subject>Tetrazoles</subject><issn>1070-4280</issn><issn>1608-3393</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp1UE1Lw0AQXUTBWv0B3ha8Gp39arLHqq0KhQqt0lvYJBuTGrN1d4PUP-bdX-aGCh7E07x5894bZhA6JXBBCOOXCwIxcJoAhQAIXe2hARlBEjEm2X7AgY36-SE6cm4NAJxwNkBm3LxsG-Vr02JTYhEtusz52ndeF3ipvVUfptEOv9e-wk_K1qZzeNzkpjKNw3WLyTmNbuq8aow12leq1T3rK40frHa6zXWfezVlX58TT-fH6KBUjdMnP3WIHqeT5fVdNJvf3l-PZ1FOGVlFRAJnCgQripHSCWVFLInIklImSsS8kEpxCQIgZzyDmDKRiYyxjISrQlewITrb5W6seeu08-nadLYNK1PKOREjKWMeVGSnyq1xzuoy3dj6VdltSiDt_5r--Wvw0J3HBW37rO1v8v-mb6MaeGg</recordid><startdate>20200701</startdate><enddate>20200701</enddate><creator>Egorov, S. A.</creator><creator>Ishchenko, M. A.</creator><creator>Prokopovich, Ya. V.</creator><creator>Ivanova, V. I.</creator><general>Pleiades Publishing</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20200701</creationdate><title>Alkylation of 5-Substituted Tetrazoles with Various Alcohols in 1,2-Dichloroethane in the Presence of BF3·Et2O</title><author>Egorov, S. A. ; Ishchenko, M. A. ; Prokopovich, Ya. V. ; Ivanova, V. I.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c231X-19043a053dd6ae823d7915b8f98a574d9aa490500c34b07235b5b33b1414723d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alcohol</topic><topic>Alkylation</topic><topic>Benzyl alcohol</topic><topic>Boron</topic><topic>Butanol</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Dichloroethane</topic><topic>Diethyl ether</topic><topic>Organic Chemistry</topic><topic>Regioselectivity</topic><topic>Substitutes</topic><topic>Tetrazoles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Egorov, S. A.</creatorcontrib><creatorcontrib>Ishchenko, M. A.</creatorcontrib><creatorcontrib>Prokopovich, Ya. V.</creatorcontrib><creatorcontrib>Ivanova, V. I.</creatorcontrib><collection>CrossRef</collection><jtitle>Russian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Egorov, S. A.</au><au>Ishchenko, M. A.</au><au>Prokopovich, Ya. V.</au><au>Ivanova, V. I.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Alkylation of 5-Substituted Tetrazoles with Various Alcohols in 1,2-Dichloroethane in the Presence of BF3·Et2O</atitle><jtitle>Russian journal of organic chemistry</jtitle><stitle>Russ J Org Chem</stitle><date>2020-07-01</date><risdate>2020</risdate><volume>56</volume><issue>7</issue><spage>1196</spage><epage>1203</epage><pages>1196-1203</pages><issn>1070-4280</issn><eissn>1608-3393</eissn><abstract>The alkylation of 1
H
-tetrazole, 5-methyl-1
H
-tetrazole, and 5-phenyl-1
H
-tetrazole with primary, secondary, and tertiary alcohols, including benzylic and allylic ones, have been studied in 1,2-dichloroethane in the presence of boron trifluoride–diethyl ether complex. Neither primary nor secondary saturated alcohols alkylated tetrazoles in the given system. Tertiary alcohols such
tert
-butyl alcohol and adamantan-1-ol reacted with unsubstituted and 5-substituted tetrazoles to give 70–85% of the corresponding 2-alkyl-5-R-tetrazoles with high regioselectivity. The alkylation of 1
H
-tetrazole with benzyl alcohol afforded 55% of 2-benzyl-2
H
-tetrazole as the only product. The alkylation of 1
H
-tetrazole with various allylic alcohols led to the formation of mixtures of 2-alkyl-2
H
-tetrazoles with isomeric alkyl substituents.</abstract><cop>Moscow</cop><pub>Pleiades Publishing</pub><doi>10.1134/S107042802007012X</doi><tpages>8</tpages></addata></record> |
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| language | eng |
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| source | SpringerNature Journals |
| subjects | Alcohol Alkylation Benzyl alcohol Boron Butanol Chemistry Chemistry and Materials Science Dichloroethane Diethyl ether Organic Chemistry Regioselectivity Substitutes Tetrazoles |
| title | Alkylation of 5-Substituted Tetrazoles with Various Alcohols in 1,2-Dichloroethane in the Presence of BF3·Et2O |
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