{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,29]],"date-time":"2026-08-29T03:49:52Z","timestamp":1787975392602,"version":"build-2784847793"},"reference-count":34,"publisher":"Wiley","issue":"26","license":[{"start":{"date-parts":[[2009,5,27]],"date-time":"2009-05-27T00:00:00Z","timestamp":1243382400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2009,6,15]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p><jats:bold>Bulking up:<\/jats:bold> The thermal barrier to rearrangement of a <jats:italic>vic<\/jats:italic>\u2010disulfoxide is significantly increased through steric buttressing about the (O)S\uf8ffS(O) bond. Whereas the title compounds represent the most thermally stable <jats:italic>vic<\/jats:italic>\u2010disulfoxides known to date, they also undergo a novel photomediated epimerization at room temperature (see scheme).<jats:boxed-text content-type=\"graphic\" position=\"anchor\"><jats:graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" mimetype=\"image\/gif\" position=\"anchor\" specific-use=\"enlarged-web-image\" xlink:href=\"graphic\/mcontent.gif\"><jats:alt-text>magnified image<\/jats:alt-text><\/jats:graphic><\/jats:boxed-text><\/jats:p>","DOI":"10.1002\/anie.200901788","type":"journal-article","created":{"date-parts":[[2009,5,28]],"date-time":"2009-05-28T00:20:28Z","timestamp":1243470028000},"page":"4832-4835","source":"Crossref","is-referenced-by-count":29,"title":["2,7\u2010Di\u2010<i>tert<\/i>\u2010butylnaphtho[1,8\u2010<i>cd<\/i>][1,2]dithiole 1,2\u2010dioxides: Thermally Stable, Photochemically Active <i>vic<\/i>\u2010Disulfoxides"],"prefix":"10.1002","volume":"48","author":[{"given":"Richard\u2005S.","family":"Grainger","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bhaven","family":"Patel","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Benson\u2005M.","family":"Kariuki","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2009,6,9]]},"reference":[{"key":"e_1_2_2_1_2","unstructured":"For reviews see:"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00060a002"},{"key":"e_1_2_2_3_2","first-page":"1","volume-title":"Reviews on Heteroatom Chemistry, Vol.\u200521","author":"Lacombe S. M.","year":"1999"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.5059\/yukigoseikyokaishi.64.395"},{"key":"e_1_2_2_5_2","unstructured":"\u00a0"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00410a051"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00385a035"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00350a049"},{"key":"e_1_2_2_9_2","unstructured":"\u00a0"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00023a088"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00061a004"},{"key":"e_1_2_2_12_2","unstructured":"\u00a0"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9915955"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(00)00435-6"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol049031f"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol052570f"},{"key":"e_1_2_2_17_2","unstructured":"\u00a0"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(02)01014-6"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0354591"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp026888q"},{"key":"e_1_2_2_21_2","unstructured":"\u00a0"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo01023a001"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol016678g"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/1099-0682(200105)2001:5<1183::AID-EJIC1183>3.0.CO;2-I"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.3891\/acta.chem.scand.53-0710"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.3987\/S(B)-1982-01-0041"},{"key":"e_1_2_2_27_2","unstructured":"Analytical data for13:Rf=0.31 (8:2n\u2010hexane\/EtOAc); m.p.\u2005178\u2013180\u2009\u00b0C (EtOAc);1H\u2005NMR (300\u2005MHz CDCl3):\u03b4=1.70 (s 18\u2009H; C(CH3)3) 7.81 (d 3J(H H)=8.6\u2005Hz 2\u2009H; ArH) 8.05\u2005ppm (d 3J(H H)=8.6\u2005Hz 2\u2009H; ArH);13C\u2005NMR (75\u2005MHz CDCl3):\u03b4=33.2 (CH3) 38.0 (C) 127.4 (CH) 132.2 (CH) 132.7 (C) 138.7 (C) 139.5 (C) 155.1\u2005ppm (C); IR (KBr):${\\tilde \\nu }$=2959 1367 1117 1067 1040\u2005cm\u22121; HRMS (EI) calcd for C18H22O2S2(M+):334.1061; found: 334.1045. Crystallographic data for13: C18H22O2S2 Mr=334.48 T=200(2)\u2005K \u03bb=0.67030\u2005\u00c5 triclinic ${P\\bar 1}$ a=8.7247(16)\u2005\u00c5 b=9.4724(18)\u2005\u00c5 c=10.642(2)\u2005\u00c5 \u03b1=97.649(3)\u00b0 \u03b2=107.070(2)\u00b0 \u03b3=92.469(3)\u00b0 V=830.1(3)\u2005\u00c53 Z=2 \u03c3cal=1.338\u2005Mg\u2009m\u22123 \u03bc=0.325\u2005mm\u22121 crystal size=0.10\u00d70.10\u00d70.05\u2005mm3 \u03b8max=30.06\u00b0 reflections collected=10\u2009683 independent reflections=5577 R(int)=0.0680 finalR1 [I>2\u03c3(I)]=0.0711 finalwR2 [I>2\u03c3(I)]=0.1793 R1 (all data)=0.0964 wR2 (all data)=0.2017 residual electron density=0.595\u2005e\u2009\u00c5\u22123. The S2O2site shows disorder with 87\/13\u2009% occupancy for O(1)\u2010S(1)\u2010S(2)\u2010O(2)\/O(1a)\u2010S(1a)\u2010S(2a)\u2010O(2a)."},{"key":"e_1_2_2_28_2","unstructured":"CCDC\u2005714447 (9) 714448 (19) 714449 (12) 714450 (15) 714451 (13) 714452 (14) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre viawww.ccdc.cam.ac.uk\/data_request\/cif."},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01061a048"},{"key":"e_1_2_2_30_2","unstructured":"Analytical data for14:Rf0.15 (8:2 60\u201380 petroleum ether\/EtOAc); m.p.\u2005172\u2013174\u2009\u00b0C;1H\u2005NMR (300\u2005MHz CDCl3):\u03b4=1.76 (s 18\u2009H; C(CH3)3) 7.81 (d 3J(H H)=8.7\u2005Hz 2\u2009H; ArH) 7.98\u2005ppm (d 3J(H H)=8.7\u2005Hz 2\u2009H; ArH);13C\u2005NMR (75\u2005MHz CDCl3):\u03b4=33.0 (CH3) 38.3 (C) 127.3 (CH) 131.7 (CH) 131.8 (C) 135.9 (C) 137.4 (C) 154.9\u2005ppm (C); IR (KBr):${\\tilde \\nu }$=2961 2925 1116 1099 1068 1042\u2005cm\u22121; HRMS (EI) calcd for C18H22O2S2(M+):334.1061; found: 334.1066. Crystallographic data for14: C18H22O2S2 Mr=334.48 T=296(2)\u2005K \u03bb=1.54178\u2005\u00c5 triclinic ${P\\bar 1}$ a=8.6970(4)\u2005\u00c5 b=9.5037(4)\u2005\u00c5 c=10.6581(4)\u2005\u00c5 \u03b1=97.635(3)\u00b0 \u03b2=107.551(2)\u00b0 \u03b3=91.727(3)\u00b0 V=830.18(6)\u2005\u00c53 Z=2 \u03c3cal=1.338\u2005Mg\u2009m\u22123 \u03bc=2.934\u2005mm\u22121 crystal size=0.30\u00d70.20\u00d70.20\u2005mm3 \u03b8max=65.74\u00b0 reflections collected=5460 independent reflections=2557 R(int)=0.0267 finalR1 [I>2\u03c3(I)]=0.0429 finalwR2 [I>2\u03c3(I)]=0.1148 R1 (all data)=0.0469 wR2 (all data)=0.1183 residual electron density=0.752\u2005e\u2009\u00c5\u22123."},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00109a042"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja017228m"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/hc.20055"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.200700824"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.200901788","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.200901788","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,28]],"date-time":"2023-09-28T22:31:06Z","timestamp":1695940266000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.200901788"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,6,9]]},"references-count":34,"journal-issue":{"issue":"26","published-print":{"date-parts":[[2009,6,15]]}},"alternative-id":["10.1002\/anie.200901788"],"URL":"https:\/\/doi.org\/10.1002\/anie.200901788","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2009,6,9]]}}}