Reaction of N-Haloamide. XX. Bromo-formyloxylation of α, β-Unsaturated Esters with N, N-Dibromobenzenesulfonamide and Formic Acid
α, β-Unsaturated esters were made to react with N, N-dibromobenzenesulfonamide and formic acid in chloroform to give bromo-formyloxyesters. Methyl acrylate (1a), ethyl crotonate (2a), ethyl trans-cinnamate (3a), methyl tiglate (4a), methyl methacrylate (5a), and methyl phenylacrylate (6a) gave methy...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1974/07/25, Vol.22(7), pp.1646-1651 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | UENO, YOSHIO YAMASAKI, AKEMI TERAUCHI, HIROMI TAKEMURA, SHOJI |
| description | α, β-Unsaturated esters were made to react with N, N-dibromobenzenesulfonamide and formic acid in chloroform to give bromo-formyloxyesters. Methyl acrylate (1a), ethyl crotonate (2a), ethyl trans-cinnamate (3a), methyl tiglate (4a), methyl methacrylate (5a), and methyl phenylacrylate (6a) gave methyl 2-bromo-3-formyloxypropionate (1b), ethyl erythro-2-bromo-3-formyloxybutyrate (2b), ethyl erythro-2-bromo-3-formyloxy-3-phenylpropionate (3b), methyl erythro-2-bromo-3-formyloxy-2-methylbutyrate (4b), a mixture of methyl 3-bromo-2-formyloxy-2-methylpropionate (5b) and methyl 2-bromo-3-formyloxy-2-methylpropionate (5c), and methyl 3-bromo-2-formyloxy-2-phenylpropionate (6b) respectively in good yields. |
| doi_str_mv | 10.1248/cpb.22.1646 |
| format | Article |
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Methyl acrylate (1a), ethyl crotonate (2a), ethyl trans-cinnamate (3a), methyl tiglate (4a), methyl methacrylate (5a), and methyl phenylacrylate (6a) gave methyl 2-bromo-3-formyloxypropionate (1b), ethyl erythro-2-bromo-3-formyloxybutyrate (2b), ethyl erythro-2-bromo-3-formyloxy-3-phenylpropionate (3b), methyl erythro-2-bromo-3-formyloxy-2-methylbutyrate (4b), a mixture of methyl 3-bromo-2-formyloxy-2-methylpropionate (5b) and methyl 2-bromo-3-formyloxy-2-methylpropionate (5c), and methyl 3-bromo-2-formyloxy-2-phenylpropionate (6b) respectively in good yields.</description><subject>Benzenesulfonates</subject><subject>Bromine</subject><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>Esters</subject><subject>Formates</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Sulfonamides</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1974</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkMtu1DAUhi0EKkNhxRrJKzY0qW9xnGXphSJVRUJU6s5y7GPqKokHO1E7bHkieJA-EwkzLQsfL_7vfNL5EXpLSUmZUId23ZaMlVQK-QytKBd1UTHGn6MVIaQpGJf8JXqV8y0hrCI130N7QnBRNXSFfn0FY8cQBxw9vizOTRdNHxyU-Pq6xB9T7GPhY-o3XbzfdOaRfPh9gB_-FFdDNuOUzAgOn-YRUsZ3YbzBlwez6yS0y3oLw08YIE-dj8M_NzaDw2ezNFh8ZIN7jV5402V4s_v30dXZ6bfj8-Liy6fPx0cXhZ0vkEXjau8obxVhirqGUF8Da0E1shXUCNZKyb2wwhAhXa2qhitvJQGpKKGWKr6P3m-96xR_TJBH3YdsoevMAHHKWrFKifnN4IctaFPMOYHX6xR6kzaaEr1UrufKNWN6qXym3-20U9uDe2J3Hc_5yTa_zaP5Dk-5SWOwHSwu2lRq8dXbsWj_xzcmaRj4X12WlXg</recordid><startdate>1974</startdate><enddate>1974</enddate><creator>UENO, YOSHIO</creator><creator>YAMASAKI, AKEMI</creator><creator>TERAUCHI, HIROMI</creator><creator>TAKEMURA, SHOJI</creator><general>The Pharmaceutical Society of Japan</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>7X8</scope></search><sort><creationdate>1974</creationdate><title>Reaction of N-Haloamide. XX. Bromo-formyloxylation of α, β-Unsaturated Esters with N, N-Dibromobenzenesulfonamide and Formic Acid</title><author>UENO, YOSHIO ; YAMASAKI, AKEMI ; TERAUCHI, HIROMI ; TAKEMURA, SHOJI</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3636-9d7fd13b80281d901f7e2be896b41a42b663f4c4a046d785938fc60e68101c183</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1974</creationdate><topic>Benzenesulfonates</topic><topic>Bromine</topic><topic>Chemical Phenomena</topic><topic>Chemistry</topic><topic>Esters</topic><topic>Formates</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Sulfonamides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>UENO, YOSHIO</creatorcontrib><creatorcontrib>YAMASAKI, AKEMI</creatorcontrib><creatorcontrib>TERAUCHI, HIROMI</creatorcontrib><creatorcontrib>TAKEMURA, SHOJI</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>UENO, YOSHIO</au><au>YAMASAKI, AKEMI</au><au>TERAUCHI, HIROMI</au><au>TAKEMURA, SHOJI</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Reaction of N-Haloamide. XX. Bromo-formyloxylation of α, β-Unsaturated Esters with N, N-Dibromobenzenesulfonamide and Formic Acid</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1974</date><risdate>1974</risdate><volume>22</volume><issue>7</issue><spage>1646</spage><epage>1651</epage><pages>1646-1651</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>α, β-Unsaturated esters were made to react with N, N-dibromobenzenesulfonamide and formic acid in chloroform to give bromo-formyloxyesters. Methyl acrylate (1a), ethyl crotonate (2a), ethyl trans-cinnamate (3a), methyl tiglate (4a), methyl methacrylate (5a), and methyl phenylacrylate (6a) gave methyl 2-bromo-3-formyloxypropionate (1b), ethyl erythro-2-bromo-3-formyloxybutyrate (2b), ethyl erythro-2-bromo-3-formyloxy-3-phenylpropionate (3b), methyl erythro-2-bromo-3-formyloxy-2-methylbutyrate (4b), a mixture of methyl 3-bromo-2-formyloxy-2-methylpropionate (5b) and methyl 2-bromo-3-formyloxy-2-methylpropionate (5c), and methyl 3-bromo-2-formyloxy-2-phenylpropionate (6b) respectively in good yields.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>4434591</pmid><doi>10.1248/cpb.22.1646</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 1974/07/25, Vol.22(7), pp.1646-1651 |
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| language | eng |
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| source | J-STAGE Free; MEDLINE; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | Benzenesulfonates Bromine Chemical Phenomena Chemistry Esters Formates Magnetic Resonance Spectroscopy Mass Spectrometry Sulfonamides |
| title | Reaction of N-Haloamide. XX. Bromo-formyloxylation of α, β-Unsaturated Esters with N, N-Dibromobenzenesulfonamide and Formic Acid |
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