{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T00:39:47Z","timestamp":1760315987050,"version":"build-2065373602"},"reference-count":25,"publisher":"Wiley","issue":"20","license":[{"start":{"date-parts":[[2003,10,10]],"date-time":"2003-10-10T00:00:00Z","timestamp":1065744000000},"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":[[2003,10,17]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Even unsubstituted butadiene adds to sulfur dioxide in the hetero\u2010Diels\u2013Alder mode more rapidly than in the chelotropic mode. The sultine can be observed in equilibrium with the diene and the sulfur dioxide only at low temperature and in the presence of CF<jats:sub>3<\/jats:sub>COOH. Crystals of 4,5\u2010dialkyl\u2010sultine resulting from the SO<jats:sub>2<\/jats:sub> addition to 1,2\u2010dimethylidenecyclohexane have been obtained at \u2212100\u2009\u00b0C and analyzed by X\u2010ray diffraction. Quantum chemical calculations have shown that hyperconjugative interactions within the sulfinyl moiety are responsible for the anomeric effects observed in sultines that prefer pseudo\u2010chair conformations with pseudo\u2010axial S\uf8feO bonds.<\/jats:p>","DOI":"10.1002\/chem.200304932","type":"journal-article","created":{"date-parts":[[2003,10,10]],"date-time":"2003-10-10T19:07:13Z","timestamp":1065812833000},"page":"4911-4915","source":"Crossref","is-referenced-by-count":13,"title":["The Hetero\u2010Diels\u2013Alder Addition of Sulfur Dioxide: The Pseudo\u2010Chair Conformation of a 4,5\u2010Dialkylsultine"],"prefix":"10.1002","volume":"9","author":[{"given":"Dean","family":"Markovic","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Elena","family":"Roversi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rosario","family":"Scoppelliti","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Pierre","family":"Vogel","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rub\u00e9n","family":"Meana","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jos\u00e9 A.","family":"Sordo","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2003,10,10]]},"reference":[{"key":"e_1_2_7_1_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00049a076"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00081a045"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00114a039"},{"key":"e_1_2_7_4_2","unstructured":"\u00a0"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja982565p"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/1522-2675(200203)85:3<712::AID-HLCA712>3.0.CO;2-5"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/1522-2675(200203)85:3<733::AID-HLCA733>3.0.CO;2-U"},{"key":"e_1_2_7_7_3","doi-asserted-by":"publisher","DOI":"10.1002\/1522-2675(200203)85:3<761::AID-HLCA761>3.0.CO;2-Q"},{"key":"e_1_2_7_7_4","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3765(20000515)6:10<1858::AID-CHEM1858>3.0.CO;2-U"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1039\/b103096p"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3765(20020315)8:6<1336::AID-CHEM1336>3.0.CO;2-R"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo981679g"},{"volume-title":"Introduction to Computational Chemistry","year":"1999","author":"Jensen F.","key":"e_1_2_7_11_2"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo010998w"},{"key":"e_1_2_7_13_2","unstructured":"Gaussian 98 Revision A.6 M. J. Frisch G. W. Trucks H. B. Schlegel G. E. Scuseria M. A. Robb J. R. Cheeseman V. G. Zakrzewski J. A. Montgomery Jr. R. E. Stratmann J. C. Burant S. Dapprich J. M. Millam A. D. Daniels K. N. Kudin M. C. Strain O. Farkas J. Tomasi V. Barone M. Cossi R. Cammi B. Mennucci C. Pomelli C. Adamo S. Clifford J. Ochterski G. A. Petersson P. Y. Ayala Q. Cui K. Morokuma D. K. Malick A. D. Rabuck K. Raghavachari J. B. Foresman J. Cioslowski J. V. Ortiz B. B. Stefanov G. Liu A. Liashenko P. Piskorz I. Komaromi R. Gomperts R. L. Martin D. J. Fox T. Keith M. A. Al\u2010Laham C. Y. Peng A. Nanayakkara C. Gonzalez M. Challacombe P. M. W. Gill B. Johnson W. Chen M. W. Wong J. L. Andres C. Gonzalez M. Head\u2010Gordon E. S. Replogle and J. A. Pople Gaussian Inc. Pittsburgh PA 1998."},{"volume-title":"Statistical Thermodynamics","year":"1997","author":"McQuarrie D. A.","key":"e_1_2_7_14_2"},{"key":"e_1_2_7_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00013a010"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00028a019"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp980229p"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00088a005"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00204a024"},{"key":"e_1_2_7_20_2","unstructured":"The corresponding crystalline sulfolene (1 3 4 5 6 7\u2010hexahydrobenzo[c]\u2010thiophen 2 2\u2010oxide) was obtained when the reaction was carried out at \u221250\u2009\u00b0C. X\u2010ray data of this compound are given in the Supporting Information."},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/j100785a001"},{"key":"e_1_2_7_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00810a059"},{"key":"e_1_2_7_22_3","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)91534-5"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.200304932","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.200304932","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T13:52:03Z","timestamp":1760277123000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.200304932"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2003,10,10]]},"references-count":25,"journal-issue":{"issue":"20","published-print":{"date-parts":[[2003,10,17]]}},"alternative-id":["10.1002\/chem.200304932"],"URL":"https:\/\/doi.org\/10.1002\/chem.200304932","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"type":"print","value":"0947-6539"},{"type":"electronic","value":"1521-3765"}],"subject":[],"published":{"date-parts":[[2003,10,10]]}}}