Deuterium and tritium labeling with the zinc-sodium iodide method
Primary and secondary hydroxyl groups can be replaced by deuterium or tritium when the corresponding sulfonate esters are reduced with zinc, sodium iodide, and deuterium or tritium oxide in 1,2-dimethoxyethane. The method tolerates a variety of other reducible functionalities, namely, ..cap alpha..,...
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| Veröffentlicht in: | J. Org. Chem.; (United States) 1983-07, Vol.48 (13), p.2233-2237 |
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| container_title | J. Org. Chem.; (United States) |
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| creator | Turecek, Frantisek Veres, Karel Kocovsky, Pavel Pouzar, Vladimir Fajkos, Jan |
| description | Primary and secondary hydroxyl groups can be replaced by deuterium or tritium when the corresponding sulfonate esters are reduced with zinc, sodium iodide, and deuterium or tritium oxide in 1,2-dimethoxyethane. The method tolerates a variety of other reducible functionalities, namely, ..cap alpha..,..beta..-enone, ketone, and ester. The labeling can be conducted with a high regiospecificity in the presence of enolizable hydrogens. The method is less satisfactory for a stereospecific replacement of secondary hydroxyl groups, yielding mixtures of stereoisomers and olefins as byproducts. The distribution of the stereoisomers depends on the rate of configurational inversion in the intermediary iodides arising by displacement of the original tosyloxy group. Deuterium NMR spectra and their use in the configurational assignment are discussed. |
| doi_str_mv | 10.1021/jo00161a019 |
| format | Article |
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The method tolerates a variety of other reducible functionalities, namely, ..cap alpha..,..beta..-enone, ketone, and ester. The labeling can be conducted with a high regiospecificity in the presence of enolizable hydrogens. The method is less satisfactory for a stereospecific replacement of secondary hydroxyl groups, yielding mixtures of stereoisomers and olefins as byproducts. The distribution of the stereoisomers depends on the rate of configurational inversion in the intermediary iodides arising by displacement of the original tosyloxy group. Deuterium NMR spectra and their use in the configurational assignment are discussed.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo00161a019</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>400702 - Radiochemistry & Nuclear Chemistry- Properties of Radioactive Materials ; ALKALI METAL COMPOUNDS ; ALKANES ; BETA DECAY RADIOISOTOPES ; BETA-MINUS DECAY RADIOISOTOPES ; CHEMICAL REACTIONS ; DEUTERIUM ; ELEMENTS ; ETHANE ; HALIDES ; HALOGEN COMPOUNDS ; HYDROCARBONS ; HYDROGEN ISOTOPES ; INORGANIC PHOSPHORS ; IODIDES ; IODINE COMPOUNDS ; ISOTOPES ; ISOTOPIC EXCHANGE ; LABELLED COMPOUNDS ; LABELLING ; LIGHT NUCLEI ; MAGNETIC RESONANCE ; METALS ; NUCLEAR MAGNETIC RESONANCE ; NUCLEI ; ODD-EVEN NUCLEI ; ODD-ODD NUCLEI ; ORGANIC COMPOUNDS ; ORGANIC SULFUR COMPOUNDS ; PHOSPHORS ; RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY ; RADIOISOTOPES ; REDUCTION ; RESONANCE ; SODIUM COMPOUNDS ; SODIUM IODIDES ; STABLE ISOTOPES ; STEREOCHEMISTRY ; SULFONATES ; TRITIUM ; USES ; YEARS LIVING RADIOISOTOPES ; ZINC</subject><ispartof>J. 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Org. Chem.; (United States)</title><addtitle>J. Org. Chem</addtitle><description>Primary and secondary hydroxyl groups can be replaced by deuterium or tritium when the corresponding sulfonate esters are reduced with zinc, sodium iodide, and deuterium or tritium oxide in 1,2-dimethoxyethane. The method tolerates a variety of other reducible functionalities, namely, ..cap alpha..,..beta..-enone, ketone, and ester. The labeling can be conducted with a high regiospecificity in the presence of enolizable hydrogens. The method is less satisfactory for a stereospecific replacement of secondary hydroxyl groups, yielding mixtures of stereoisomers and olefins as byproducts. The distribution of the stereoisomers depends on the rate of configurational inversion in the intermediary iodides arising by displacement of the original tosyloxy group. Deuterium NMR spectra and their use in the configurational assignment are discussed.</description><subject>400702 - Radiochemistry & Nuclear Chemistry- Properties of Radioactive Materials</subject><subject>ALKALI METAL COMPOUNDS</subject><subject>ALKANES</subject><subject>BETA DECAY RADIOISOTOPES</subject><subject>BETA-MINUS DECAY RADIOISOTOPES</subject><subject>CHEMICAL REACTIONS</subject><subject>DEUTERIUM</subject><subject>ELEMENTS</subject><subject>ETHANE</subject><subject>HALIDES</subject><subject>HALOGEN COMPOUNDS</subject><subject>HYDROCARBONS</subject><subject>HYDROGEN ISOTOPES</subject><subject>INORGANIC PHOSPHORS</subject><subject>IODIDES</subject><subject>IODINE COMPOUNDS</subject><subject>ISOTOPES</subject><subject>ISOTOPIC EXCHANGE</subject><subject>LABELLED COMPOUNDS</subject><subject>LABELLING</subject><subject>LIGHT NUCLEI</subject><subject>MAGNETIC RESONANCE</subject><subject>METALS</subject><subject>NUCLEAR MAGNETIC RESONANCE</subject><subject>NUCLEI</subject><subject>ODD-EVEN NUCLEI</subject><subject>ODD-ODD NUCLEI</subject><subject>ORGANIC COMPOUNDS</subject><subject>ORGANIC SULFUR COMPOUNDS</subject><subject>PHOSPHORS</subject><subject>RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY</subject><subject>RADIOISOTOPES</subject><subject>REDUCTION</subject><subject>RESONANCE</subject><subject>SODIUM COMPOUNDS</subject><subject>SODIUM IODIDES</subject><subject>STABLE ISOTOPES</subject><subject>STEREOCHEMISTRY</subject><subject>SULFONATES</subject><subject>TRITIUM</subject><subject>USES</subject><subject>YEARS LIVING RADIOISOTOPES</subject><subject>ZINC</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1983</creationdate><recordtype>article</recordtype><recordid>eNptkEtLAzEUhYMoWKsr_8DgxoWM5jmPZalPLFhtXYc0c-OktjOSZPDx680wIi68m3PhfhzOPQgdE3xOMCUX6xZjkhGFSbmDRkRQnGYl5rtohDGlKaMZ20cH3q9xHCHECE0uoQvgbLdNVFMlwdnQ7xu1go1tXpJ3G-ok1JB82Uanvq36q41SQbKFULfVIdozauPh6EfH6Pn6ajm9TWcPN3fTySxVjBYhXQkqsDDAqSl4TFMaowkwXJYUK250zkSfPOerKis044RTAEZKwkxhONNsjE4G39YHK722AXSt26YBHaTICKO4jNDZAGnXeu_AyDdnt8p9SoJlX5H8U1Gk04G2PsDHL6rcq8xylgu5nC_kYk4LQu8f5VPkTwdeaR-NOtfEh_91_gauoXMg</recordid><startdate>19830701</startdate><enddate>19830701</enddate><creator>Turecek, Frantisek</creator><creator>Veres, Karel</creator><creator>Kocovsky, Pavel</creator><creator>Pouzar, Vladimir</creator><creator>Fajkos, Jan</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>OTOTI</scope></search><sort><creationdate>19830701</creationdate><title>Deuterium and tritium labeling with the zinc-sodium iodide method</title><author>Turecek, Frantisek ; Veres, Karel ; Kocovsky, Pavel ; Pouzar, Vladimir ; Fajkos, Jan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a328t-b52505fe42f840029ffc1e309920a4fc735161a74bd68c34142ee31913f8f43c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1983</creationdate><topic>400702 - Radiochemistry & Nuclear Chemistry- Properties of Radioactive Materials</topic><topic>ALKALI METAL COMPOUNDS</topic><topic>ALKANES</topic><topic>BETA DECAY RADIOISOTOPES</topic><topic>BETA-MINUS DECAY RADIOISOTOPES</topic><topic>CHEMICAL REACTIONS</topic><topic>DEUTERIUM</topic><topic>ELEMENTS</topic><topic>ETHANE</topic><topic>HALIDES</topic><topic>HALOGEN COMPOUNDS</topic><topic>HYDROCARBONS</topic><topic>HYDROGEN ISOTOPES</topic><topic>INORGANIC PHOSPHORS</topic><topic>IODIDES</topic><topic>IODINE COMPOUNDS</topic><topic>ISOTOPES</topic><topic>ISOTOPIC EXCHANGE</topic><topic>LABELLED COMPOUNDS</topic><topic>LABELLING</topic><topic>LIGHT NUCLEI</topic><topic>MAGNETIC RESONANCE</topic><topic>METALS</topic><topic>NUCLEAR MAGNETIC RESONANCE</topic><topic>NUCLEI</topic><topic>ODD-EVEN NUCLEI</topic><topic>ODD-ODD NUCLEI</topic><topic>ORGANIC COMPOUNDS</topic><topic>ORGANIC SULFUR COMPOUNDS</topic><topic>PHOSPHORS</topic><topic>RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY</topic><topic>RADIOISOTOPES</topic><topic>REDUCTION</topic><topic>RESONANCE</topic><topic>SODIUM COMPOUNDS</topic><topic>SODIUM IODIDES</topic><topic>STABLE ISOTOPES</topic><topic>STEREOCHEMISTRY</topic><topic>SULFONATES</topic><topic>TRITIUM</topic><topic>USES</topic><topic>YEARS LIVING RADIOISOTOPES</topic><topic>ZINC</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Turecek, Frantisek</creatorcontrib><creatorcontrib>Veres, Karel</creatorcontrib><creatorcontrib>Kocovsky, Pavel</creatorcontrib><creatorcontrib>Pouzar, Vladimir</creatorcontrib><creatorcontrib>Fajkos, Jan</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>OSTI.GOV</collection><jtitle>J. Org. Chem.; (United States)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Turecek, Frantisek</au><au>Veres, Karel</au><au>Kocovsky, Pavel</au><au>Pouzar, Vladimir</au><au>Fajkos, Jan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Deuterium and tritium labeling with the zinc-sodium iodide method</atitle><jtitle>J. Org. Chem.; (United States)</jtitle><addtitle>J. Org. Chem</addtitle><date>1983-07-01</date><risdate>1983</risdate><volume>48</volume><issue>13</issue><spage>2233</spage><epage>2237</epage><pages>2233-2237</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Primary and secondary hydroxyl groups can be replaced by deuterium or tritium when the corresponding sulfonate esters are reduced with zinc, sodium iodide, and deuterium or tritium oxide in 1,2-dimethoxyethane. The method tolerates a variety of other reducible functionalities, namely, ..cap alpha..,..beta..-enone, ketone, and ester. The labeling can be conducted with a high regiospecificity in the presence of enolizable hydrogens. The method is less satisfactory for a stereospecific replacement of secondary hydroxyl groups, yielding mixtures of stereoisomers and olefins as byproducts. The distribution of the stereoisomers depends on the rate of configurational inversion in the intermediary iodides arising by displacement of the original tosyloxy group. Deuterium NMR spectra and their use in the configurational assignment are discussed.</abstract><cop>United States</cop><pub>American Chemical Society</pub><doi>10.1021/jo00161a019</doi><tpages>5</tpages></addata></record> |
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| ispartof | J. Org. Chem.; (United States), 1983-07, Vol.48 (13), p.2233-2237 |
| issn | 0022-3263 1520-6904 |
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| recordid | cdi_crossref_primary_10_1021_jo00161a019 |
| source | ACS Publications |
| subjects | 400702 - Radiochemistry & Nuclear Chemistry- Properties of Radioactive Materials ALKALI METAL COMPOUNDS ALKANES BETA DECAY RADIOISOTOPES BETA-MINUS DECAY RADIOISOTOPES CHEMICAL REACTIONS DEUTERIUM ELEMENTS ETHANE HALIDES HALOGEN COMPOUNDS HYDROCARBONS HYDROGEN ISOTOPES INORGANIC PHOSPHORS IODIDES IODINE COMPOUNDS ISOTOPES ISOTOPIC EXCHANGE LABELLED COMPOUNDS LABELLING LIGHT NUCLEI MAGNETIC RESONANCE METALS NUCLEAR MAGNETIC RESONANCE NUCLEI ODD-EVEN NUCLEI ODD-ODD NUCLEI ORGANIC COMPOUNDS ORGANIC SULFUR COMPOUNDS PHOSPHORS RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY RADIOISOTOPES REDUCTION RESONANCE SODIUM COMPOUNDS SODIUM IODIDES STABLE ISOTOPES STEREOCHEMISTRY SULFONATES TRITIUM USES YEARS LIVING RADIOISOTOPES ZINC |
| title | Deuterium and tritium labeling with the zinc-sodium iodide method |
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