{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,20]],"date-time":"2025-10-20T17:35:17Z","timestamp":1760981717798,"version":"build-2065373602"},"reference-count":16,"publisher":"Wiley","issue":"12","license":[{"start":{"date-parts":[[1994,12,1]],"date-time":"1994-12-01T00:00:00Z","timestamp":786240000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Lipids"],"published-print":{"date-parts":[[1994,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A novel 1\u2010pyrroline fatty acid ester isomer [<jats:italic>viz.<\/jats:italic> 8\u2010(5\u2010hexyl\u20101\u2010pyrrolin\u20102\u2010yl)octanoate] has been synthesized from methyl ricinoleate by two routes with an overall yield of 42 and 30%, respectively. Most of the reactions are carried out under concomitant ultrasonic irradiation (20 KHz,<jats:italic>ca.<\/jats:italic> 53 watts\/cm<jats:sup>2<\/jats:sup>). Under such a reaction condition, the reaction time is considerably shortened, and product yields are high. Dehydrobromination under concomitant ultrasonic irradiation of methyl 9,10\u2010dibromo\u201012\u2010hydroxyoctadecanoate with KOH in EtOH furnishes methyl 12\u2010hydroxy\u20109\u2010octadecynoate (66%) within 15 min. Hydration of the latter under ultrasound with mercury(II)acetate in aqueous tetrahydrofuran yields exclusively methyl 12\u2010hydroxy\u20109\u2010oxo\u2010octadecanoate (95%) in 30 min. The hydroxy group in the latter compound is transformed to the azido function<jats:italic>via<\/jats:italic> the mesylate, and treatment of the azido\u2010oxo intermediate (methyl 12\u2010azido\u20109\u2010oxooctadecanoate) with Ph<jats:sub>3<\/jats:sub>P under ultrasonic irradiation furnishes the requisite 1\u2010pyrroline fatty acid ester (77%). The same azido\u2010oxo intermediate has also been obtained by the oxidation of methyl 12\u2010azido\u20109\u2010<jats:italic>cis<\/jats:italic>\u2010octadecenoate using benzoquinone and a catalytic amount of Pd(II)chloride in aqueous tetrahydrofuran under concomitant ultrasonic irradiation (90 min) to give the product in 45% yield. The latter reaction does not take place even under prolonged silent stirring of the reaction mixture.<\/jats:p>","DOI":"10.1007\/bf02536258","type":"journal-article","created":{"date-parts":[[2006,12,5]],"date-time":"2006-12-05T03:55:48Z","timestamp":1165290948000},"page":"889-892","source":"Crossref","is-referenced-by-count":20,"title":["Ultrasound in fatty acid chemistry: Synthesis of a 1\u2010pyrroline fatty acid ester isomer from methyl ricinoleate"],"prefix":"10.1002","volume":"29","author":[{"given":"Marcel S. F.","family":"Lie Ken Jie","sequence":"first","affiliation":[{"name":"Department of Chemistry The University of Hong Kong Pokfulam Road Hong Kong"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"M. S. K.","family":"Syed\u2010Rahmatullah","sequence":"additional","affiliation":[{"name":"Department of Chemistry The University of Hong Kong Pokfulam Road Hong Kong"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"C. K.","family":"Lam","sequence":"additional","affiliation":[{"name":"Department of Chemistry The University of Hong Kong Pokfulam Road Hong Kong"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"P.","family":"Kalluri","sequence":"additional","affiliation":[{"name":"Department of Chemistry The University of Hong Kong Pokfulam Road Hong Kong"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[1994,12]]},"reference":[{"key":"e_1_2_2_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(76)88001-5"},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(82)80044-6"},{"key":"e_1_2_2_4_1","doi-asserted-by":"publisher","DOI":"10.1001\/archderm.1957.01550160001001"},{"key":"e_1_2_2_5_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.130.3373.449"},{"key":"e_1_2_2_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)87182-3"},{"key":"e_1_2_2_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)71506-1"},{"key":"e_1_2_2_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00208a016"},{"key":"e_1_2_2_9_1","doi-asserted-by":"crossref","unstructured":"Fraser R.R. andPassannanti S.(1976)Synthesis 540\u2013541.","DOI":"10.1055\/s-1976-24115"},{"key":"e_1_2_2_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)81697-5"},{"key":"e_1_2_2_11_1","first-page":"421","volume":"1","author":"Lie Ken Jie M.S.F.","year":"1991","journal-title":"J. Chem. Soc. Perkin Trans."},{"key":"e_1_2_2_12_1","doi-asserted-by":"crossref","unstructured":"Gunstone F.D.(1954)J. Chem. Soc. 1611\u20131616.","DOI":"10.1039\/jr9540001611"},{"key":"e_1_2_2_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/ac50153a010"},{"key":"e_1_2_2_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/0009-3084(73)90051-0"},{"key":"e_1_2_2_15_1","doi-asserted-by":"crossref","unstructured":"Crombie L. andJacklin A.G.(1955)J. Chem. Soc. 1740\u20131748.","DOI":"10.1039\/jr9550001740"},{"key":"e_1_2_2_16_1","doi-asserted-by":"crossref","unstructured":"Lambert P.H. Vaultier M. andCarrie R.(1982)J. Chem. Soc. Chem. Commun. 1224\u20131225.","DOI":"10.1039\/C39820001224"},{"key":"e_1_2_2_17_1","first-page":"1","volume":"1","author":"Lie Ken Jie M.S.F.","year":"1989","journal-title":"J. Chem. Soc. 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