{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,5]],"date-time":"2026-02-05T09:38:07Z","timestamp":1770284287082,"version":"3.49.0"},"reference-count":51,"publisher":"Wiley","issue":"43","license":[{"start":{"date-parts":[[2013,9,11]],"date-time":"2013-09-11T00:00:00Z","timestamp":1378857600000},"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":[[2013,10,18]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The syntheses of a zwitterionic base\u2010stabilized digermadistannacyclobutadiene and tetragermacyclobutadiene supported by amidinates and low\u2010valent germanium amidinate substituents are described. The reaction of the amidinate Ge<jats:sup>I<\/jats:sup> dimer, [LGe:]<jats:sub>2<\/jats:sub> (<jats:bold>1<\/jats:bold>, L=PhC(N<jats:italic>t<\/jats:italic>Bu)<jats:sub>2<\/jats:sub>), with two equivalents of the amidinate tin(II) chloride, [LSnCl] (<jats:bold>2<\/jats:bold>), and KC<jats:sub>8<\/jats:sub> in tetrahydrofuran (THF) at room temperature afforded a mixture of the zwitterionic base\u2010stabilized digermadistannacyclobutadiene, [L<jats:sub>2<\/jats:sub>Ge<jats:sub>2<\/jats:sub>Sn<jats:sub>2<\/jats:sub>L\u2032<jats:sub>2<\/jats:sub>] (<jats:bold>3<\/jats:bold>; L\u2032=LGe:), and the bis(amidinate) tin(II) compound, [L<jats:sub>2<\/jats:sub>Sn:] (<jats:bold>4<\/jats:bold>). Compound <jats:bold>3<\/jats:bold> can also be prepared by the reaction of <jats:bold>1<\/jats:bold> with [L<jats:sup>Ar<\/jats:sup>SnCl] (<jats:bold>5<\/jats:bold>, L<jats:sup>Ar<\/jats:sup>=<jats:italic>t<\/jats:italic>BuC(NAr)<jats:sub>2<\/jats:sub>, Ar=2,6\u2010<jats:italic>i<\/jats:italic>Pr<jats:sub>2<\/jats:sub>C<jats:sub>6<\/jats:sub>H<jats:sub>3<\/jats:sub>) in THF at room temperature. Moreover, the reaction of <jats:bold>1<\/jats:bold> with the \u201conio\u2010substituent transfer\u201d reagent [4\u2010NMe<jats:sub>2<\/jats:sub>\u2010C<jats:sub>5<\/jats:sub>H<jats:sub>4<\/jats:sub>NSiMe<jats:sub>3<\/jats:sub>]OTf (<jats:bold>8<\/jats:bold>) in THF and 4\u2010(<jats:italic>N<\/jats:italic>,<jats:italic>N<\/jats:italic>\u2010dimethylamino)pyridine (DMAP) at room temperature afforded a mixture of the zwitterionic base\u2010stabilized tetragermacyclobutadiene, [L<jats:sub>4<\/jats:sub>Ge<jats:sub>6<\/jats:sub>] (<jats:bold>9<\/jats:bold>), the amidinium triflate, [PhC(NH<jats:italic>t<\/jats:italic>Bu)<jats:sub>2<\/jats:sub>]OTf (<jats:bold>10<\/jats:bold>), and Me<jats:sub>3<\/jats:sub>SiSiMe<jats:sub>3<\/jats:sub> (<jats:bold>11<\/jats:bold>). X\u2010ray structural data and theoretical studies show conclusively that compounds <jats:bold>3<\/jats:bold> and <jats:bold>9<\/jats:bold> have a planar and rhombic charge\u2010separated structure. They are also nonaromatic.<\/jats:p>","DOI":"10.1002\/chem.201300447","type":"journal-article","created":{"date-parts":[[2013,9,11]],"date-time":"2013-09-11T15:34:08Z","timestamp":1378913648000},"page":"14726-14731","source":"Crossref","is-referenced-by-count":29,"title":["Zwitterionic Base\u2010Stabilized Digermadistannacyclobutadiene and Tetragermacyclobutadiene"],"prefix":"10.1002","volume":"19","author":[{"given":"Hui\u2010Xian","family":"Yeong","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hong\u2010Wei","family":"Xi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yongxin","family":"Li","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sophy Bhasi","family":"Kunnappilly","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Bozhen","family":"Chen","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kai\u2010Chung","family":"Lau","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hajime","family":"Hirao","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kok Hwa","family":"Lim","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Cheuk\u2010Wai","family":"So","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2013,9,11]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39720001268"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00789a088"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00785a056"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00783a066"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1199906"},{"key":"e_1_2_6_7_2","unstructured":"\u00a0"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja050938y"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200600338"},{"key":"e_1_2_6_9_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200600338"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0dt00009d"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.200701046"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0318481"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201102201"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/om800714f"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.201000803"},{"key":"e_1_2_6_16_2","unstructured":"THF (15\u2005mL) was added to a mixture of2(0.809\u2005g 2.10\u2005mmol) and KC8(0.340\u2005g 2.52\u2005mmol) at room temperature and the resulting reaction mixture was stirred overnight. The insoluble precipitate was filtered off the volatiles of the filtrate were removed in vacuo and the residue was extracted with Et2O. After filtration and concentration of the filtrate 4was afforded as colorless crystals."},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja204344e"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic3005954"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1039\/b706663e"},{"key":"e_1_2_6_20_2","unstructured":"Compound6can be synthesized by the reaction of two equivalents of LArLi with SnCl2in Et2O. It has been analyzed by X\u2010ray crystallography and NMR spectroscopy. For details see the Supporting Information. With the119Sn\u2005NMR signal of compound6in hand we can illustrate that compound6was formed by the reaction of1and5in THF."},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200460039"},{"key":"e_1_2_6_21_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200460039"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00013a001"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/om020855f"},{"key":"e_1_2_6_24_2","unstructured":"\u00a0"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic00029a035"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00014a014"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(99)00386-1"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1039\/b900592g"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19860981024"},{"key":"e_1_2_6_29_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198609171"},{"key":"e_1_2_6_30_2","unstructured":"When the reaction was performed without DMAP a mixture of unidentified compounds was formed which was confirmed by1H\u2005NMR spectroscopy."},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201300255"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja2033475"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/9780470669266"},{"key":"e_1_2_6_34_2","unstructured":"For details of theoretical studies and references see the Supporting Information."},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(68)88057-3"},{"key":"e_1_2_6_36_2","unstructured":"\u00a0"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol016217v"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja960582d"},{"key":"e_1_2_6_39_2","unstructured":"\u00a0"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201005866"},{"key":"e_1_2_6_40_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201005866"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja200462y"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1017\/CBO9780511614569"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19980202)110:3<282::AID-ANGE282>3.0.CO;2-R"},{"key":"e_1_2_6_43_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19980216)37:3<270::AID-ANIE270>3.0.CO;2-P"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201103443"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja802502b"},{"key":"e_1_2_6_46_2","unstructured":"G.\u2005M. 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