{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T13:43:41Z","timestamp":1787060621312,"version":"build-2736575974"},"reference-count":13,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2004,2,28]],"date-time":"2004-02-28T00:00:00Z","timestamp":1077926400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The mono-epoxidation of geraniol by dimethyldioxirane was carried out invarious solvents. In all cases, the product ratios for the 2,3 and 6,7 mono-epoxides werein agreement with literature values. Kinetic studies were carried out at 23 oC in thefollowing dried solvent systems: acetone (k2 = 1.49 M-1s-1), carbon tetrachloride\/acetone(9\/1, k2=2.19 M-1s-1), and methanol\/acetone (9\/1, k2 = 17 M-1s-1). Individual k2 valueswere calculated for epoxidation of the 2,3 and 6,7 positions in geraniol. The non-conjugated diene system was modeled employing two simple independent alkenes:2-methyl-2-pentene and 3-methyl-2-buten-1-ol by determining the respective k2 valuesfor epoxidation in various solvents. The kinetic results for each independent alkeneshowed that the relative reactivity of the two epoxidation sites in geraniol as a function ofsolvent was not simply a summation of the independent alkene systems.<\/jats:p>","DOI":"10.3390\/90300117","type":"journal-article","created":{"date-parts":[[2008,10,25]],"date-time":"2008-10-25T13:32:11Z","timestamp":1224941531000},"page":"117-124","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Kinetics of the Epoxidation of Geraniol and Model Systems by Dimethyldioxirane"],"prefix":"10.3390","volume":"9","author":[{"given":"A. L.","family":"Baumstark","sequence":"first","affiliation":[{"name":"Department of Chemistry, Center for Biotech and Drug Design, Georgia State University, Atlanta, Georgia 30303-3083, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"P. J.","family":"Franklin","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Center for Biotech and Drug Design, Georgia State University, Atlanta, Georgia 30303-3083, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"P. C.","family":"Vasquez","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Center for Biotech and Drug Design, Georgia State University, Atlanta, Georgia 30303-3083, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"B. S.","family":"Crow","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Center for Biotech and Drug Design, Georgia State University, Atlanta, Georgia 30303-3083, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2004,2,28]]},"reference":[{"key":"ref_1","unstructured":"For selected reviews see:\n\t\t\t\t\t\t\t\t\t\t\t\t  \n\t\t\t\t\t\t\t\t\t\t\t\t    a)\u00a0\n\t\t\t\t\t\t\t\t\t\t\t\t\t\n\t\t\t\t\t\t\t\t\t\t            \n\t\t\t\t\t\t\t\t\t\t              Curci\n\t\t\t\t\t\t\t\t\t\t              R.\n\t\t\t\t\t\t\t\t\t\t            \n\t\t\t\t\t\t\t\t\t\t\t\t\t\n\t\t\t\t\t\t\t\t\t\t\t\t\t\u201cAdvances in Oxygenated Processes\u201d\n\t\t\t\t\t\t\t\t\t\t\t\t\tVol. 2\n\t\t\t\t\t\t\t\t\t\t\t\t\t\n\t\t\t\t\t\t\t\t\t\t            \n\t\t\t\t\t\t\t\t\t\t              Baumstark\n\t\t\t\t\t\t\t\t\t\t              A.\n\t\t\t\t\t\t\t\t\t\t            \n\t\t\t\t\t\t\t\t\t\t\t\t\t\n\t\t\t\t\t\t\t\t\t\t\t\t\tJAI Press\n\t\t\t\t\t\t\t\t\t\t            Greenwich, CT\n\t\t\t\t\t\t\t\t\t\t            1990\n\t\t\t\t\t\t\t\t\t\t\t\t  \n\t\t\t\t\t\t\t\t\t\t\t\t  \n\t\t\t\t\t\t\t\t\t\t\t\t    b)\u00a0\n\t\t\t\t\t\t\t\t\t\t\t\t\t\n\t\t\t\t\t\t\t\t\t\t            \n\t\t\t\t\t\t\t\t\t\t              Adam\n\t\t\t\t\t\t\t\t\t\t              W\n\t\t\t\t\t\t\t\t\t\t            \n\t\t\t\t\t\t\t\t\t\t\t\t\t\n\t\t\t\t\t\t\t\t\t\t              Hadjiarapogolonu\n\t\t\t\t\t\t\t\t\t\t              L.\n\t\t\t\t\t\t\t\t\t\t            \n\t\t\t\t\t\t\t\t\t\t\t\t\t\n\t\t\t\t\t\t\t\t\t\t              Curci\n\t\t\t\t\t\t\t\t\t\t              R.\n\t\t\t\t\t\t\t\t\t\t            \n\t\t\t\t\t\t\t\t\t\t\t\t\t\n\t\t\t\t\t\t\t\t\t\t              Mello\n\t\t\t\t\t\t\t\t\t\t              R.\n\t\t\t\t\t\t\t\t\t\t            \n\t\t\t\t\t\t\t\t\t\t\t\t\t\n\t\t\t\t\t\t\t\t\t\t\t\t\tChapt. 4\n\t\t\t\t\t\t\t\t\t\t\t\t\t\u201cOrganic Peroxides,\u201d\n\t\t\t\t\t\t\t\t\t\t\t\t\t\n\t\t\t\t\t\t\t\t\t\t            \n\t\t\t\t\t\t\t\t\t\t              Adam\n\t\t\t\t\t\t\t\t\t\t              W.\n\t\t\t\t\t\t\t\t\t\t            \n\t\t\t\t\t\t\t\t\t\t\t\t\t\n\t\t\t\t\t\t\t\t\t\t\t\t\tWiley and Sons\n\t\t\t\t\t\t\t\t\t\t            Chichester, England\n\t\t\t\t\t\t\t\t\t\t            1992\n\t\t\t\t\t\t\t\t\t\t\t\t  \n\t\t\t\t\t\t\t\t\t\t\t\t  \n\t\t\t\t\t\t\t\t\t\t\t\t    c)\u00a0\n\t\t\t\t\t\t\t\t\t\t\t\t    \n\t\t\t\t\t\t\t\t\t\t            \n\t\t\t\t\t\t\t\t\t\t              Adam\n\t\t\t\t\t\t\t\t\t\t              W.\n\t\t\t\t\t\t\t\t\t\t            \n\t\t\t\t\t\t\t\t\t\t\t\t\t\n\t\t\t\t\t\t\t\t\t\t              Hadjiarapogolonu\n\t\t\t\t\t\t\t\t\t\t              L.\n\t\t\t\t\t\t\t\t\t\t            \n\t\t\t\t\t\t\t\t\t\t\t\t    \n\t\t\t\t\t\t\t\t\t\t\t\t    Top. 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Soc., 120, 1872.","DOI":"10.1021\/ja972800o"},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Michelena-Baez, E., Navarro-Eisenstein, A.M., Banks, H.D., Vasquez, P.C., and Baumstark, A.L. (2000). Het. Comm., 6, 119.","DOI":"10.1515\/HC.2000.6.2.119"},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Onoda, T., Shirai, R., Koiso, Y., and Iwasaki, S. (1996). Tetrahedron, 52, 14543.","DOI":"10.1016\/0040-4020(96)00899-X"},{"key":"ref_10","unstructured":"Chavnan, S.M.S., Parkash, S., and Mohaptra, P.P. (1997). Indian J. Chem. Sect. B, 312."},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Palombi, L., Bonadies, F., and Scetti, A. (1997). Tetrahedron, 53, 11369.","DOI":"10.1016\/S0040-4020(97)00718-7"},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Robinson, P.L., Barry, C.N., Kelly, J.W., and Evans, S.A. (1985). J. Am. Chem. Soc., 107, 5210.","DOI":"10.1021\/ja00304a030"},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Gilbert, M., Ferrer, M., S\u00e1nchez-Baeza, F., and Messequer, A. (1997). Tetrahedron, 53, 8643.","DOI":"10.1016\/S0040-4020(97)00533-4"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/9\/3\/117\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T22:26:03Z","timestamp":1760221563000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/9\/3\/117"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2004,2,28]]},"references-count":13,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2004,3]]}},"alternative-id":["90300117"],"URL":"https:\/\/doi.org\/10.3390\/90300117","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2004,2,28]]}}}