{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T14:30:45Z","timestamp":1786977045941,"version":"build-2736575974"},"reference-count":97,"publisher":"Wiley","issue":"36","license":[{"start":{"date-parts":[[2021,8,3]],"date-time":"2021-08-03T00:00:00Z","timestamp":1627948800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100005156","name":"Alexander von Humboldt-Stiftung","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100005156","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2021,9]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    The synthesis of element\u2212carbon double bonds is of great importance for the development and understanding of reactive \u03c0\u2010bonded systems in chemistry. The seven\u2010membered heterocyclic system\n                    <jats:bold>4\u2009b<\/jats:bold>\n                    is readily made by internal C\u2212H activation at a pendent isopropyl methyl group of the respective [(IPr)C\n                    <jats:sub>6<\/jats:sub>\n                    F\n                    <jats:sub>5<\/jats:sub>\n                    BH]\n                    <jats:sup>+<\/jats:sup>\n                    borenium ion. Subsequent deprotonation with the IMes carbene gives the neutral cyclic boraalkene system\n                    <jats:bold>5\u2009b<\/jats:bold>\n                    . The B=C double bond in compound\n                    <jats:bold>5\u2009b<\/jats:bold>\n                    adds carbon dioxide, CS\n                    <jats:sub>2<\/jats:sub>\n                    , sulfur dioxide, phenyl isocyanate, an acetylenic ester or two NO molecules to give the corresponding four\u2010membered ring annulated heterocycles. With sulfur or selenium\n                    <jats:bold>5\u2009b<\/jats:bold>\n                    gives the respective three\u2010membered ring systems. N\n                    <jats:sub>2<\/jats:sub>\n                    O reacts with\n                    <jats:bold>5\u2009b<\/jats:bold>\n                    to give a mixture of the related oxaborirane\n                    <jats:bold>18<\/jats:bold>\n                    and a unique [B]OH containing diazoalkane product\n                    <jats:bold>19<\/jats:bold>\n                    .\n                  <\/jats:p>","DOI":"10.1002\/anie.202106724","type":"journal-article","created":{"date-parts":[[2021,7,4]],"date-time":"2021-07-04T22:10:25Z","timestamp":1625436625000},"page":"19905-19911","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":37,"title":["Formation and Cycloaddition Reactions of a Reactive Boraalkene Stabilized Internally by\n                    <i>N<\/i>\n                    \u2010Heterocyclic Carbene"],"prefix":"10.1002","volume":"60","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2761-3766","authenticated-orcid":false,"given":"Chaohuang","family":"Chen","sequence":"first","affiliation":[{"name":"Organisch-Chemisches Institut Westf\u00e4lische Wilhelms-Universit\u00e4t M\u00fcnster  Corrensstra\u00dfe 40 48149 M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6709-3673","authenticated-orcid":false,"given":"Constantin G.","family":"Daniliuc","sequence":"additional","affiliation":[{"name":"Organisch-Chemisches Institut Westf\u00e4lische Wilhelms-Universit\u00e4t M\u00fcnster  Corrensstra\u00dfe 40 48149 M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5196-2491","authenticated-orcid":false,"given":"Gerald","family":"Kehr","sequence":"additional","affiliation":[{"name":"Organisch-Chemisches Institut Westf\u00e4lische Wilhelms-Universit\u00e4t M\u00fcnster  Corrensstra\u00dfe 40 48149 M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2488-3699","authenticated-orcid":false,"given":"Gerhard","family":"Erker","sequence":"additional","affiliation":[{"name":"Organisch-Chemisches Institut Westf\u00e4lische Wilhelms-Universit\u00e4t M\u00fcnster  Corrensstra\u00dfe 40 48149 M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,8,3]]},"reference":[{"key":"e_1_2_6_1_1","unstructured":"For reviews see:"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar00081a003"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1007\/3-540-48956-8_2"},{"key":"e_1_2_6_4_1","unstructured":"See for examples:"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00774a047"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00789a068"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00242a064"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200702299"},{"key":"e_1_2_6_8_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200702299"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC02223C"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202100919"},{"key":"e_1_2_6_10_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202100919"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202002125"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202002125"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201200063"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201200063"},{"key":"e_1_2_6_13_1","unstructured":"For reviews see:"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199309851"},{"key":"e_1_2_6_14_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19931050706"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9408989"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100133q"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2020.213647"},{"key":"e_1_2_6_18_2","volume-title":"PATAI\u2032S Chemistry of Functional Groups","author":"Devillard M.","year":"2021"},{"key":"e_1_2_6_18_3","doi-asserted-by":"crossref","unstructured":"https:\/\/doi.org\/10.1002\/9780470682531.pat0972.","DOI":"10.1002\/9780470682531.pat0972"},{"key":"e_1_2_6_19_1","unstructured":"For reviews see:"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00953A"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.202100192"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19861191228"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol100534s"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB01591G"},{"key":"e_1_2_6_25_1","unstructured":"See for examples:"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198308771"},{"key":"e_1_2_6_26_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19830951111"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198813701"},{"key":"e_1_2_6_27_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19881001032"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199010301"},{"key":"e_1_2_6_28_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19901020925"},{"key":"e_1_2_6_29_1","unstructured":"See for examples:"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198504161"},{"key":"e_1_2_6_30_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19850970527"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198813311"},{"key":"e_1_2_6_31_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19881001012"},{"key":"e_1_2_6_32_1","unstructured":"See for examples:"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19871200631"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19891220402"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199216031"},{"key":"e_1_2_6_35_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19921041232"},{"key":"e_1_2_6_36_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19891220607"},{"key":"e_1_2_6_37_1","unstructured":"\u00a0"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201412006"},{"key":"e_1_2_6_38_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201412006"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201506368"},{"key":"e_1_2_6_39_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201506368"},{"key":"e_1_2_6_40_1","unstructured":"\u00a0"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201608994"},{"key":"e_1_2_6_41_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201608994"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b07823"},{"key":"e_1_2_6_43_1","unstructured":"\u00a0"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202009353"},{"key":"e_1_2_6_44_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202009353"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr200133c"},{"key":"e_1_2_6_46_1","unstructured":"For review see:"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CS00763F"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201500198"},{"key":"e_1_2_6_48_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201500198"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2021.03.010"},{"key":"e_1_2_6_50_1","unstructured":"For reviews see:"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic502231m"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00079"},{"key":"e_1_2_6_53_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1221138"},{"key":"e_1_2_6_54_1","unstructured":"\u00a0"},{"key":"e_1_2_6_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo01084a635"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01059a065"},{"key":"e_1_2_6_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00034a006"},{"key":"e_1_2_6_58_1","unstructured":"For comparison see:"},{"key":"e_1_2_6_59_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7DT04350C"},{"key":"e_1_2_6_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201802117"},{"key":"e_1_2_6_60_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201802117"},{"key":"e_1_2_6_61_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202103427"},{"key":"e_1_2_6_61_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202103427"},{"key":"e_1_2_6_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c10078"},{"key":"e_1_2_6_63_1","doi-asserted-by":"publisher","DOI":"10.1002\/zaac.200300396"},{"key":"e_1_2_6_64_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201601691"},{"key":"e_1_2_6_64_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201601691"},{"key":"e_1_2_6_65_1","unstructured":"For reviews see:"},{"key":"e_1_2_6_66_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.196305651"},{"key":"e_1_2_6_66_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19630751304"},{"key":"e_1_2_6_67_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202003115"},{"key":"e_1_2_6_67_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202003115"},{"key":"e_1_2_6_68_1","unstructured":"\u00a0"},{"key":"e_1_2_6_69_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00339C"},{"key":"e_1_2_6_70_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-021-00675-5"},{"key":"e_1_2_6_71_1","unstructured":"See for comparison:"},{"key":"e_1_2_6_72_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201101622"},{"key":"e_1_2_6_72_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201101622"},{"key":"e_1_2_6_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr500520s"},{"key":"e_1_2_6_74_1","unstructured":"Deposition Numbers 2059122 (for4b) 2059123 (for5a) 2059124 (for5b) 2059125 (for6b) 2059126 (for8) 2059127 (for9a) 2091486 (for9b) 2091487 (for9c) 2059128 (for10) 2059129 (for11) 2059134 (for12) 2059135 (for13) 2059137 (for14eq) 2059136 (14ax) 2062438 (for15eq) 2059138 (for15ax) 2059139 (for16) 2059140 (for18) and 2059141 (for19) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures servicewww.ccdc.cam.ac.uk\/structures."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202106724","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202106724","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202106724","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,20]],"date-time":"2023-08-20T10:33:01Z","timestamp":1692527581000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202106724"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,8,3]]},"references-count":97,"journal-issue":{"issue":"36","published-print":{"date-parts":[[2021,9]]}},"alternative-id":["10.1002\/anie.202106724"],"URL":"https:\/\/doi.org\/10.1002\/anie.202106724","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,8,3]]},"assertion":[{"value":"2021-05-19","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-08-03","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}