Unsymmetrically Substituted 9,10-Dihydro-9,10-diboraanthracenes as Versatile Building Blocks for Boron-Doped π-Conjugated Systems
作者:Estera Januszewski、Andreas Lorbach、Rekha Grewal、Michael Bolte、Jan W. Bats、Hans-Wolfram Lerner、Matthias Wagner
DOI:10.1002/chem.201101701
日期:2011.11.4
10‐diboraanthracene adduct (Me2S)HB(C6H4)2BH(SMe2) (1) with 0.5 equiv of H2O leads to formation of the borinic acid anhydride [(Me2S)HB(C6H4)2B]2O (2) and thereby provides access to the field of unsymmetrically substituted 9,10‐dihydro‐9,10‐diboraanthracenes. Compound 2 reacts with tBuCCH to give the corresponding vinyl derivative in an essentially quantitative conversion. Subsequent cleavage of the B‐O‐B
以0.5当量的H 2 O定向水解9,10-dihydro-9,10-diboraanthracene加合物(Me 2 S)HB(C 6 H 4)2 BH(SMe 2)(1)导致形成硼酸酐[(Me 2 S)HB(C 6 H 4)2 B] 2 O(2),从而提供了进入不对称取代的9,10-dihydro-9,10-diboraanthracenes领域的途径。化合物2与t反应BuCCH基本上定量转化得到相应的乙烯基衍生物。的B-O-B通过桥的LiAlH随后裂解4与地层化硼酸官能度是可能的,但伴随着局部乙 C(乙烯基)键的降解。当使用相关的均三甲苯基衍生物[MesB(C 6 H 4)2 B] 2 O(7)时,这种情况会改变,该衍生物可以通过用1当量的NaCl处理从BrB(C 6 H 4)2 BBr(6)合成。 MesMgBr和随后的水解。7与LiAlH 4的反应在四氢呋喃(THF)中提供Li