NUCLEOPHILIC REACTIONS OF SEMIIONIC OXYGEN. II. A NOVEL PREPARATION OF ETHYL GLYOXYLATE FROM ETHYL BROMOACETATE AND DIMETHYL SULFOXIDE. THE STOICHIOMETRY AND THE SULFUR-CONTAINING BY-PRODUCTS
The reaction of excess dimethyl sulfoxide with ethyl romoacetate produce ethyl glyoxylate, hy rogen bromide, and dimethyl sulfide. A convenient preparation of ethyl glyoxylate in yields averaging 70% was developed. The generality of the dimethyl sulfoxide oxidation was demonstrated by applying it to...
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| creator | Tien ,Jack M Hunsberger,I Moyer |
| description | The reaction of excess dimethyl sulfoxide with ethyl romoacetate produce ethyl glyoxylate, hy rogen bromide, and dimethyl sulfide. A convenient preparation of ethyl glyoxylate in yields averaging 70% was developed. The generality of the dimethyl sulfoxide oxidation was demonstrated by applying it to a variety of alpha-halogenated acids and esters. An ionic mechanism for this oxidation is suggested which involves nucleophilic displacement of the halogen by the sulfoxide oxygen. A number of earlierreported reactions of sulfoxides al o appear to depend on the nucleophilic nature of their oxygen atoms. It is suggested that other compounds containing semiionic oxygen will exhibit analogous reactions. (Author) |
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THE STOICHIOMETRY AND THE SULFUR-CONTAINING BY-PRODUCTS</title><source>DTIC Technical Reports</source><creator>Tien ,Jack M ; Hunsberger,I Moyer</creator><creatorcontrib>Tien ,Jack M ; Hunsberger,I Moyer ; FORDHAM UNIV BRONX N Y</creatorcontrib><description>The reaction of excess dimethyl sulfoxide with ethyl romoacetate produce ethyl glyoxylate, hy rogen bromide, and dimethyl sulfide. A convenient preparation of ethyl glyoxylate in yields averaging 70% was developed. The generality of the dimethyl sulfoxide oxidation was demonstrated by applying it to a variety of alpha-halogenated acids and esters. An ionic mechanism for this oxidation is suggested which involves nucleophilic displacement of the halogen by the sulfoxide oxygen. A number of earlierreported reactions of sulfoxides al o appear to depend on the nucleophilic nature of their oxygen atoms. It is suggested that other compounds containing semiionic oxygen will exhibit analogous reactions. (Author)</description><language>eng</language><subject>ACETALS ; BROMIDES ; CHEMICAL REACTIONS ; DISPLACEMENT REACTIONS ; ESTERS ; ETHYL RADICALS ; GLYOXYLIC ACID ; HALIDES ; HALOGEN COMPOUNDS ; IONS ; METHYL RADICALS ; OXIDATION ; OXIDATION REDUCTION REACTIONS ; OXYGEN ; PREPARATION ; REACTION KINETICS ; REDUCTION ; SULFOXIDES ; SYNTHESIS</subject><creationdate>1959</creationdate><rights>APPROVED FOR PUBLIC RELEASE</rights><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,776,881,27546,27547</link.rule.ids><linktorsrc>$$Uhttps://apps.dtic.mil/sti/citations/AD0264111$$EView_record_in_DTIC$$FView_record_in_$$GDTIC$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>Tien ,Jack M</creatorcontrib><creatorcontrib>Hunsberger,I Moyer</creatorcontrib><creatorcontrib>FORDHAM UNIV BRONX N Y</creatorcontrib><title>NUCLEOPHILIC REACTIONS OF SEMIIONIC OXYGEN. II. A NOVEL PREPARATION OF ETHYL GLYOXYLATE FROM ETHYL BROMOACETATE AND DIMETHYL SULFOXIDE. THE STOICHIOMETRY AND THE SULFUR-CONTAINING BY-PRODUCTS</title><description>The reaction of excess dimethyl sulfoxide with ethyl romoacetate produce ethyl glyoxylate, hy rogen bromide, and dimethyl sulfide. A convenient preparation of ethyl glyoxylate in yields averaging 70% was developed. The generality of the dimethyl sulfoxide oxidation was demonstrated by applying it to a variety of alpha-halogenated acids and esters. An ionic mechanism for this oxidation is suggested which involves nucleophilic displacement of the halogen by the sulfoxide oxygen. A number of earlierreported reactions of sulfoxides al o appear to depend on the nucleophilic nature of their oxygen atoms. It is suggested that other compounds containing semiionic oxygen will exhibit analogous reactions. (Author)</description><subject>ACETALS</subject><subject>BROMIDES</subject><subject>CHEMICAL REACTIONS</subject><subject>DISPLACEMENT REACTIONS</subject><subject>ESTERS</subject><subject>ETHYL RADICALS</subject><subject>GLYOXYLIC ACID</subject><subject>HALIDES</subject><subject>HALOGEN COMPOUNDS</subject><subject>IONS</subject><subject>METHYL RADICALS</subject><subject>OXIDATION</subject><subject>OXIDATION REDUCTION REACTIONS</subject><subject>OXYGEN</subject><subject>PREPARATION</subject><subject>REACTION KINETICS</subject><subject>REDUCTION</subject><subject>SULFOXIDES</subject><subject>SYNTHESIS</subject><fulltext>true</fulltext><rsrctype>report</rsrctype><creationdate>1959</creationdate><recordtype>report</recordtype><sourceid>1RU</sourceid><recordid>eNqFik1OwzAQRrNhgYAbsJgLJGoAsZ_ak3gkxxPZE1SvKtQfqVLVTXM_roZTumf1fXrvPVY_YTKeZHTs2UAkNMoSEkgHiQYuv2DZ5J5CA8wNIAT5Ig9jpBEjLvUSk7rsofe5tB6VoIsy3Om6XEFDunAMFiwPfyZNvpMNW2pAHUFSYeNYio35Vt5oiaZYGwmKHDj0sM71GMVORtNz9XD8Pl8PL_d9ql47UuPq_Xzaba_z6XKYt2hXb58fbdu-_6N_AYf_Stk</recordid><startdate>19590531</startdate><enddate>19590531</enddate><creator>Tien ,Jack M</creator><creator>Hunsberger,I Moyer</creator><scope>1RU</scope><scope>BHM</scope></search><sort><creationdate>19590531</creationdate><title>NUCLEOPHILIC REACTIONS OF SEMIIONIC OXYGEN. II. A NOVEL PREPARATION OF ETHYL GLYOXYLATE FROM ETHYL BROMOACETATE AND DIMETHYL SULFOXIDE. 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| source | DTIC Technical Reports |
| subjects | ACETALS BROMIDES CHEMICAL REACTIONS DISPLACEMENT REACTIONS ESTERS ETHYL RADICALS GLYOXYLIC ACID HALIDES HALOGEN COMPOUNDS IONS METHYL RADICALS OXIDATION OXIDATION REDUCTION REACTIONS OXYGEN PREPARATION REACTION KINETICS REDUCTION SULFOXIDES SYNTHESIS |
| title | NUCLEOPHILIC REACTIONS OF SEMIIONIC OXYGEN. II. A NOVEL PREPARATION OF ETHYL GLYOXYLATE FROM ETHYL BROMOACETATE AND DIMETHYL SULFOXIDE. THE STOICHIOMETRY AND THE SULFUR-CONTAINING BY-PRODUCTS |
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