Hypohalogenation of functionally substituted acetylenic norbornenes
Hypohalogenation of norbornenes containing a triple bond and various functional groups in the side chain was performed using mixtures of aqueous solutions of hydrochloric or hydrobromic acid (or sodium or potassium bromide) and hydrogen peroxide. The reaction was found to involve addition of electro...
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| Veröffentlicht in: | Russian journal of organic chemistry 2008-09, Vol.44 (9), p.1282-1290 |
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| container_title | Russian journal of organic chemistry |
| container_volume | 44 |
| creator | Veliev, M. G. Sadygov, O. A. Shatirova, M. I. Alimardanov, Kh. M. |
| description | Hypohalogenation of norbornenes containing a triple bond and various functional groups in the side chain was performed using mixtures of aqueous solutions of hydrochloric or hydrobromic acid (or sodium or potassium bromide) and hydrogen peroxide. The reaction was found to involve addition of electrophilic reagent generated
in situ
(HOBr or HOCl) at the endocyclic double bond with formation of the corresponding halohydrins. The latter underwent dehydrohalogenation by the action of alklai to give
exo
-5,6-epoxybicyclo[2.2.1]-heptane derivatives in high yields. Kinetic relations holding in the hypobromination process were established, and the initial rates and activation parameters were calculated. |
| doi_str_mv | 10.1134/S1070428008090066 |
| format | Article |
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in situ
(HOBr or HOCl) at the endocyclic double bond with formation of the corresponding halohydrins. The latter underwent dehydrohalogenation by the action of alklai to give
exo
-5,6-epoxybicyclo[2.2.1]-heptane derivatives in high yields. Kinetic relations holding in the hypobromination process were established, and the initial rates and activation parameters were calculated.</description><identifier>ISSN: 1070-4280</identifier><identifier>EISSN: 1608-3393</identifier><identifier>DOI: 10.1134/S1070428008090066</identifier><language>eng</language><publisher>Dordrecht: SP MAIK Nauka/Interperiodica</publisher><subject>Chemistry ; Chemistry and Materials Science ; Organic Chemistry</subject><ispartof>Russian journal of organic chemistry, 2008-09, Vol.44 (9), p.1282-1290</ispartof><rights>MAIK Nauka 2008</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c288t-bbd785373624dc1b3244ea784995b8fc1bc4b88a35b574def070e13c4be2a7bd3</citedby><cites>FETCH-LOGICAL-c288t-bbd785373624dc1b3244ea784995b8fc1bc4b88a35b574def070e13c4be2a7bd3</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/S1070428008090066$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1134/S1070428008090066$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids></links><search><creatorcontrib>Veliev, M. G.</creatorcontrib><creatorcontrib>Sadygov, O. A.</creatorcontrib><creatorcontrib>Shatirova, M. I.</creatorcontrib><creatorcontrib>Alimardanov, Kh. M.</creatorcontrib><title>Hypohalogenation of functionally substituted acetylenic norbornenes</title><title>Russian journal of organic chemistry</title><addtitle>Russ J Org Chem</addtitle><description>Hypohalogenation of norbornenes containing a triple bond and various functional groups in the side chain was performed using mixtures of aqueous solutions of hydrochloric or hydrobromic acid (or sodium or potassium bromide) and hydrogen peroxide. The reaction was found to involve addition of electrophilic reagent generated
in situ
(HOBr or HOCl) at the endocyclic double bond with formation of the corresponding halohydrins. The latter underwent dehydrohalogenation by the action of alklai to give
exo
-5,6-epoxybicyclo[2.2.1]-heptane derivatives in high yields. Kinetic relations holding in the hypobromination process were established, and the initial rates and activation parameters were calculated.</description><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Organic Chemistry</subject><issn>1070-4280</issn><issn>1608-3393</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><recordid>eNp9UEFOwzAQtBBIlMIDuOUDgXXsxM4RRUCRKnEAzpHtrEuqYFe2c8jvcVVuSD3taGZnNTuE3FN4oJTxxw8KAnglASS0AE1zQVa0AVky1rLLjLNcHvVrchPjHgA45WxFus1y8N9q8jt0Ko3eFd4WdnbmiNU0LUWcdUxjmhMOhTKYlgndaArng_bBocN4S66smiLe_c01-Xp5_uw25fb99a172pamkjKVWg9C1kywpuKDoZpVnKMSkrdtraXNjOFaSsVqXQs-oM2RkbJMYqWEHtia0NNdE3yMAW1_COOPCktPoT-20P9rIXuqkyfmXbfD0O_9HPJn8YzpFx78YEg</recordid><startdate>20080901</startdate><enddate>20080901</enddate><creator>Veliev, M. G.</creator><creator>Sadygov, O. A.</creator><creator>Shatirova, M. I.</creator><creator>Alimardanov, Kh. M.</creator><general>SP MAIK Nauka/Interperiodica</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20080901</creationdate><title>Hypohalogenation of functionally substituted acetylenic norbornenes</title><author>Veliev, M. G. ; Sadygov, O. A. ; Shatirova, M. I. ; Alimardanov, Kh. M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c288t-bbd785373624dc1b3244ea784995b8fc1bc4b88a35b574def070e13c4be2a7bd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Organic Chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Veliev, M. G.</creatorcontrib><creatorcontrib>Sadygov, O. A.</creatorcontrib><creatorcontrib>Shatirova, M. I.</creatorcontrib><creatorcontrib>Alimardanov, Kh. M.</creatorcontrib><collection>CrossRef</collection><jtitle>Russian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Veliev, M. G.</au><au>Sadygov, O. A.</au><au>Shatirova, M. I.</au><au>Alimardanov, Kh. M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Hypohalogenation of functionally substituted acetylenic norbornenes</atitle><jtitle>Russian journal of organic chemistry</jtitle><stitle>Russ J Org Chem</stitle><date>2008-09-01</date><risdate>2008</risdate><volume>44</volume><issue>9</issue><spage>1282</spage><epage>1290</epage><pages>1282-1290</pages><issn>1070-4280</issn><eissn>1608-3393</eissn><abstract>Hypohalogenation of norbornenes containing a triple bond and various functional groups in the side chain was performed using mixtures of aqueous solutions of hydrochloric or hydrobromic acid (or sodium or potassium bromide) and hydrogen peroxide. The reaction was found to involve addition of electrophilic reagent generated
in situ
(HOBr or HOCl) at the endocyclic double bond with formation of the corresponding halohydrins. The latter underwent dehydrohalogenation by the action of alklai to give
exo
-5,6-epoxybicyclo[2.2.1]-heptane derivatives in high yields. Kinetic relations holding in the hypobromination process were established, and the initial rates and activation parameters were calculated.</abstract><cop>Dordrecht</cop><pub>SP MAIK Nauka/Interperiodica</pub><doi>10.1134/S1070428008090066</doi><tpages>9</tpages></addata></record> |
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| subjects | Chemistry Chemistry and Materials Science Organic Chemistry |
| title | Hypohalogenation of functionally substituted acetylenic norbornenes |
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