{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T19:19:36Z","timestamp":1790018376711,"version":"4.0.1"},"reference-count":107,"publisher":"Wiley","issue":"20","license":[{"start":{"date-parts":[[2010,4,15]],"date-time":"2010-04-15T00:00:00Z","timestamp":1271289600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2010,5,25]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The first ene reactions of SO<jats:sub>2<\/jats:sub> and unfunctionalized alkenes are reported. Calculations suggest that the endergonic ene reactions of SO<jats:sub>2<\/jats:sub> with alkenes can be used to generate \u03b2,\u03b3\u2010unsaturated sulfinyl and sulfonyl compounds. Indeed, in the presence of one equivalent of BCl<jats:sub>3<\/jats:sub>, the unstable sulfinic acid form stable sulfinic acid\u22c5BCl<jats:sub>3<\/jats:sub> complexes that can be reacted in situ with NCS to generate corresponding sulfonyl chlorides, or with a base to generate corresponding sulfinates. The latter can be reacted with electrophiles to generate sulfones, or with silyl chloride to form \u03b2,\u03b3\u2010unsaturated silyl sulfinates. The sulfinic acid\u22c5BCl<jats:sub>3<\/jats:sub> complexes can be reacted with ethers that act as oxygen nucleophiles to produce corresponding sulfinic esters. Thus one\u2010pot, three\u2010component synthesis of \u03b2,\u03b3\u2010unsaturated sulfonamides, sulfinyl esters and sulfones have been developed starting from alkenes and sulfur dioxide (reagent and solvent).<\/jats:p>","DOI":"10.1002\/chem.201000164","type":"journal-article","created":{"date-parts":[[2010,4,15]],"date-time":"2010-04-15T12:34:50Z","timestamp":1271334890000},"page":"5969-5975","source":"Crossref","is-referenced-by-count":29,"title":["BCl<sub>3<\/sub>\u2010Mediated Ene Reaction of Sulfur Dioxide and Unfunctionalized Alkenes"],"prefix":"10.1002","volume":"16","author":[{"given":"Dean","family":"Markovi\u0107","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chandra\u2005M.\u2005R.","family":"Volla","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pierre","family":"Vogel","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Adri\u00e1n","family":"Varela\u2010\u00c1lvarez","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jos\u00e9\u2005A.","family":"Sordo","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2010,5,14]]},"reference":[{"key":"e_1_2_8_1_2","unstructured":"\u00a0"},{"key":"e_1_2_8_2_2","volume-title":"Sulfonamides, Vol.\u200523","author":"Weidner\u2010Wells M. 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See:"},{"key":"e_1_2_8_88_2","doi-asserted-by":"publisher","DOI":"10.1039\/b410965a"},{"key":"e_1_2_8_89_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol049135q"},{"key":"e_1_2_8_90_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00127a022"},{"key":"e_1_2_8_91_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja901565s"},{"key":"e_1_2_8_92_2","doi-asserted-by":"publisher","DOI":"10.1080\/14756360127572"},{"key":"e_1_2_8_93_2","unstructured":"17O\u2010enriched tetrahydrofuran was obtained by the reaction of 1 4\u2010diiodobutane with17O\u2010enriched water by using NaOH andnBu4NOH as bases. The17O enrichment of tetrahydrofuran was determined by17O\u2010NMR by using naturally abundant17O\u2010MeOH as a reference. It was established to be 4.6\u00b10.2\u2009%. The reaction with this labeled THF gave12showing 4.5\u00b10.2\u2009% of17O in the S\u2010O\u2010alkyl moiety. 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