2,2'bi-1,3,2-benzodithiaborole | 78336-55-7

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 2,2'bi-1,3,2-benzodithiaborole
• 英文别名: B2(1,2-S2-C6H4)2；bis(dithiocatecholato)diborane；1,1-B2(dithiocatecholate)2；1,1-B2-[1,2-S2C6H4]2；2,2'-Bi-1,3,2-benzodithiaborole；2-(1,3,2-benzodithiaborol-2-yl)-1,3,2-benzodithiaborole
• CAS: 78336-55-7
• 化学式: C₁₂H₈B₂S₄
• 分子量: 302.082
• InChiKey: BXXMVURPUJADOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7,7,8,8-四氰基对苯二醌二甲烷 、 2,2'bi-1,3,2-benzodithiaborole 以 二氯甲烷 为溶剂， 以60%的产率得到C12H4N4*C12H8B2S4, dark red
  参考文献：
  名称：

  乙硼烷（4）化合物B 2（1,2-E 2 C 6 H 4）2（E = O或S）的结晶TCNQ和TCNE加合物

  摘要：

  乙硼烷（4）化合物与电子受体TCNQ和TCNE的1∶1加合物的晶体结构，即B 2（1,2-E 2 C 6 H 4）2 ·TCNQ（E = O或S）和B 2（已经发现1,2-E 2 C 6 H 4）2 ·TCNE（E = O或S）主要显示带有各种夹层填充物的二维异分子填充图案。

  DOI：

  10.1039/a901169b
• 作为产物：
  描述：

  sodium catecholate 在 HCl 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 生成 2,2'bi-1,3,2-benzodithiaborole
  参考文献：
  名称：

  环状和不对称乙硼烷（4）化合物的合成路线

  摘要：

  1,2-B 2 Cl 2（NMe 2）2与儿茶酚二钠Na 2 [1,2-O 2 C 6 H 4 ]得到环状乙硼烷（4）化合物1,2-B 2（NMe 2）2（cat）（cat = 1,2-O 2 C 6 H 4） ，而使用硫代儿茶酸二锂Li 2 [1,2-S 2 C 6 H 4 ]得到1,1-异构体1,1-B 2（NMe 2）2（硫代催化剂）（硫代催化剂= 1,2-S 2 C 6 H 4）。两种化合物均可用于制备不对称乙硼烷（4）。

  DOI：

  10.1039/a909645k

文献信息

• Oxidative addition of boron–boron, boron–chlorine and boron–bromine bonds to platinum(0)1Dedicated to Professor Ken Wade on the occasion of his 65th birthday and in recognition of his outstanding contributions to the understanding of the chemistry of boron.1
  作者：William Clegg、Fiona J. Lawlor、Gerry Lesley、Todd B. Marder、Nicholas C. Norman、A.Guy Orpen、Michael J. Quayle、Craig R. Rice、Andrew J. Scott、Fabio E.S. Souza

  DOI：10.1016/s0022-328x(97)00233-7

  日期：1998.1

  2-O2C6Cl4)2 and B2(1,2-O2C6Br4)2 are reported together with the diborane(4) bis-amine adduct [B2(calix)(NHMe2)2] (calix=Butcalix[4]arene). B–B bond oxidative addition reactions between the platinum(0) compound [Pt(PPh3)2(η-C2H4)] and the diborane(4) compounds B2(1,2-S2C6H4)2, B2(1,2-O2C6Cl4)2 and B2(1,2-O2C6Br4)2 are also described which result in the platinum(II) bis-boryl complexes cis-[Pt(PPh3)2B(1,2-S2C6H4)}2]

  报道了新的乙硼烷（4）化合物B 2（1,2-O 2 C 6 Cl 4）2和B 2（1,2-O 2 C 6 Br 4）2的合成及光谱表征。（4）双-胺加合物[B 2（杯形）（NHMe 2）2 ]（杯=卜吨杯[4]芳烃）。铂（0）化合物[Pt（PPh 3）2（η- C 2 H 4）]和乙硼烷（4）化合物B 2（1,2-S 2 C 6 H 4）2，B 2（1,2-O 2 C 6 Cl 4）2和B 2（1,2-O 2还描述了C 6 Br 4）2，其导致铂（II）双-硼基络合物顺式-[Pt（PPh 3）2 B（1,2-S 2 C 6 H 4）} 2 ]，顺式- [Pt（PPh 3）2 B（1,2-O 2 C 6 Cl 4）} 2 ]和顺式-[Pt（PPh 3）2 B（1,2-O 2 C 6 Br 4）} 2 ]，前者两个已经通过X射线晶体学表征。此外，铂络合物[Pt（PPh 3）2（η- C 2
• Mild synthesis of diboryldiborenes by diboration of B–B triple bonds
  作者：Tobias Brückner、Rian D. Dewhurst、Theresa Dellermann、Marcel Müller、Holger Braunschweig

  DOI：10.1039/c9sc02544h

  日期：——

  A set of diboryldiborenes are prepared by the mild, catalyst-free, room-temperature diboration of the B–B triple bonds of doubly base-stabilized diborynes. Two of the product diboryldiborenes are found to be air- and water-stable in the solid state, an effect that is attributed to their high crystallinity and extreme insolubility in a wide range of solvents.

  通过双碱稳定二硼炔的 B-B 三键在室温下进行温和、无催化剂的二硼化反应，制备了一组二硼基二硼烯。发现其中两种产物二硼基二硼烯在固态下对空气和水都是稳定的，这是由于它们在各种溶剂中的高结晶度和极不溶性造成的。
• 2,2′-Bipyridyl and 1,10-phenanthroline adducts of the diborane (4) compound B2 (1,2-S2C6H4)2
  作者：Chaoyang Dai、Stuart M. Johnson、Fiona J. Lawlor、Philip Lightfoot、Todd B. Marder、Nicholas C. Norman、A.Guy Orpen、Nigel L. Pickett、Michael J. Quayle、Craig R. Rice

  DOI：10.1016/s0277-5387(98)00221-6

  日期：1998.11

  The syntheses and structures of the 2,2′-bipyridyl and 1,10-phenanthroline adducts of the diborane (4) compound B2 (1,2-S2C6H4)2 are described. In both cases, the bidentate nitrogen donor ligands bridge the B–B bond, one nitrogen being bonded to each boron.

  描述了乙硼烷（4）化合物B 2（1,2-S 2 C 6 H 4）2的2,2'-联吡啶和1,10-菲咯啉加合物的合成和结构。在这两种情况下，双齿氮供体配体桥接了B–B键，一个氮键与每个硼键合。
• Lewis-base adducts of the diborane(4) compounds B2(1,2-E2C6H4)2 (E = O or S)
  作者：William Clegg、Chaoyang Dai、Fiona J. Lawlor、Todd B. Marder、Paul Nguyen、Nicholas C. Norman、Nigel L. Pickett、William P. Power、Andrew J. Scott

  DOI：10.1039/a607440e

  日期：——

  The reactivity of the diborane(4) compounds B 2 (1,2-E 2 C 6 H 4 ) 2 (E = O or S) have been studied with respect to their ability to co-ordinate Lewis bases, specifically 4-methylpyridine (mpy) and the phosphines PMe 2 Ph and PEt 3 . Four monoadducts have been characterised by X-ray crystallography, namely B 2 (1,2-O 2 C 6 H 4 ) 2 (mpy), B 2 (1,2-S 2 C 6 H 4 ) 2 (mpy), B 2 (1,2-S 2 C 6 H 4 ) 2 (PMe 2 Ph) and B 2 (1,2-S 2 C 6 H 4 ) 2 (PEt 3 ), together with three bis adducts B 2 (1,2-O 2 C 6 H 4 ) 2 (mpy) 2 , B 2 (1,2-S 2 C 6 H 4 ) 2 (mpy) 2 and B 2 (1,2-S 2 C 6 H 4 ) 2 (PMe 2 Ph) 2 . In the former set of compounds the one base is co-ordinated to one boron centre which adopts a tetrahedral geometry, the remaining boron being trigonal planar as in the structure of the parent compound. For the bis adducts each of the two borons is co-ordinated to a mpy or phosphine with both borons tetrahedral. Bond-length changes associated with ligand co-ordination are discussed. Multinuclear solution-state NMR studies have also been performed for solutions containing B 2 (1,2-O 2 C 6 H 4 ) 2 and mpy, B 2 (1,2-S 2 C 6 H 4 ) 2 and mpy and B 2 (1,2-S 2 C 6 H 4 ) 2 and PEt 3 . All of these studies indicate that intermolecular exchange of base between the parent compound, the mono- and the bis-adducts occurs in solution together with intramolecular exchange between the two boron centres in the monoadducts. The various rates of these processes, inasmuch as they have been determined accurately, are discussed and rationalised. The monoadducts B 2 (1,2-O/S 2 C 6 H 4 ) 2 (mpy) are nominally isoelectronic with the phenonium cation.

  研究了二硼烷（4）化合物 B 2 (1,2-E 2 C 6 H 4 ) 2 (E = O 或 S) 与路易斯碱（特别是 4-甲基吡啶 (mpy) 和膦 PMe 2 Ph 和 PEt 3）配位的反应能力。通过 X 射线晶体学分析，确定了四种单加成物的特征，即 B 2 (1,2-O 2 C 6 H 4 ) 2 (mby)、B 2 (1,2-S 2 C 6 H 4 ) 2 (mby)、B 2 (1,2-S 2 C 6 H 4 ) 2 (PMe 2 Ph) 和 B 2 (1.2-S 2 C 6 H 4 ) 2 (1.2-O 2 C 6 H 4 ) 2 (mby)、2-S 2 C 6 H 4 ）2 （PEt 3 ），以及三种双加合物 B 2 （1,2-O 2 C 6 H 4 ）2 （mby）2、B 2 （1,2-S 2 C 6 H 4 ）2 （mby）2 和 B 2 （1,2-S 2 C 6 H 4 ）2 （PMe 2 Ph）2。在前一组化合物中，一个碱基与一个硼中心配位，硼中心呈四面体几何形状，其余的硼中心呈三棱锥平面，与母体化合物的结构相同。在双加合物中，两个硼分别与一个钼或膦配位，两个硼都是四面体。 我们讨论了与配体配位有关的键长变化。 我们还对含有 B 2 (1,2-O 2 C 6 H 4 ) 2 和钼的溶液、B 2 (1,2-S 2 C 6 H 4 ) 2 和钼的溶液以及 B 2 (1,2-S 2 C 6 H 4 ) 2 和 PEt 3 的溶液进行了多核溶液状态核磁共振研究。所有这些研究都表明，母体化合物、单加成物和双加成物之间的碱在溶液中发生了分子间交换，同时单加成物中的两个硼中心之间也发生了分子内交换。本文讨论了这些过程的各种速率，并将其合理化，因为这些速率已被准确测定。单加合物 B 2 (1,2-O/S 2 C 6 H 4 ) 2 (mpy) 名义上与苯鎓阳离子是等电子的。
• Bis-Catecholate, Bis-Dithiocatecholate, and Tetraalkoxy Diborane(4) Compounds:  Aspects of Synthesis and Electronic Structure
  作者：Fiona J. Lawlor、Nicholas C. Norman、Nigel L. Pickett、Edward G. Robins、Paul Nguyen、Gerry Lesley、Todd B. Marder、Jennifer A. Ashmore、Jennifer C. Green

  DOI：10.1021/ic980425a

  日期：1998.10.5

  The synthesis and characterization of a series of bis-catecholate diborane(4) compounds, B-2(1,2-O2C6H4)(2) (3), B-2(1,2-O-2-3-MeC6H3)(2) (6), B-2(1,2-O-2-4-MeC6H3)(2) (7), B-2(1,2-O-2-4-(BuC6H3)-C-t)(2) (8), B-2(1,2-O-2-3,5-(Bu2C6H2)-C-t)(2) (9), B-2(1,2-O-2-3-MeOC6H3)(2) (10), bis-ditkiocatecholate diborane(3) compounds, B-2(1,2-S2C6H4)(2) (13), B-2(1,2-S-2-4-MeC6H3)(2) (14), and tetraalkoxy diborane(4) compounds, B-2(OCH2CMe2CH2O)(2) (11) and B-2(OCMe2CMe2O)(2) (12) from B-2(NMe2)(4) (1) is described, as are the bis(NHMe2) adducts or 3 and 9, namely [B-2(1,1-O2C6H4)(2)-(NHMe2)(2)] (1) and [B-2(1,2-O-2-3,5-(Bu2C6H2)-C-t)(2)(NHMe2)(2)] (5). The latter two compounds are intermediates in thr formation of 3 and 9 from 1. Compound 1 is synthesized by reductive coupling of BCl(NMe2)(2), which in turn is prepared from reaction of BCl3 with B(NMe2)(3) in a 1:2 stoichiometry. We have also tharacterized [B2Cl4- (NHMe2)(2)] (15) formed from addition of HCl to 1 prior to complete reaction with diols, and the salt, [NH2Me2][B(1,2-O2C6H3)(2)] (16) which arises from addition of catechol to B(NMe2)(3). Thus, any B(NMe2)(3) impurity present after the preparation of 1 needs to be removed by distillation prior to reaction with alcohols. The dimer, [BCl2-(mu-NMe2)](2) (17) has also been characterized. This is formed from reaction of BCl3 with B(NMe2)(3) if a 2:1 rather than 1:2 stoichiometry is used. Photoelectron spectra of 1, 3, 8, 11, and 12 are reported along with those of the corresponding diols, catechol, 4-Bu-t-catechol, 2,2-dimethyl-1,3-propanediol. and pinacol. The ionization energies of the B-2(OR)(4) compounds follow the series 8 < 3 < 12 < 11. Replacement of O for N in the B2N4 framework increases the IE by ca. 1.65 eV, whereas the presence of an aromatic ring rather than an aliphatic chain decreases the IE by ca. 1.50 eV. The presence of electron donating Bu-t-gr oups also decreases the IE.