The protecting group-free synthesis of a versatile 1,2-azaborine synthon 5 is described. Previously inaccessible 1,2-azaborine derivatives, including the BN isostere of phenyl phenylacetate and BN1 triphenylmethane were prepared from 5 and characterized. The structural investigation of BN phenyl phenylacetate revealed the presence of a unique NH-carbonyl hydrogen bond that is not present in the corresponding carbonaceous analogue. The methyne CH in BN triphenylmethane was found to be less acidic than the corresponding proton in triphenylmethane. The gram-quantity synthesis of the parent 1,2-azaborine 4 was demonstrated, which enabled the characterization of its boiling point, density, refractive index, and its polarity on the ET(30) scale.
The protecting group-free synthesis of a versatile n class="Chemical">1,2-azaborine synthon 5n> is described. Previously inaccessible 1,2-azaborine derivatives, including the BN isostere of phenyl phenylacetate and BN1triphenylmethane were prepared from 5 and characterized. The structural investigation of BN phenyl phenylacetate revealed the presence of a unique NH-carbonyl hydrogen bond that is not present in the corresponding carbonaceous analogue. The methyne CH in BN triphenylmethane was found to be less acidic than the corresponding proton in triphenylmethane. The gram-quantity synthesis of the parent 1,2-azaborine 4 was demonstrated, which enabled the characterization of its boiling point, density, refractive index, and its polarity on the ET(30) scale.
Authors: Daniel H Knack; Jonathan L Marshall; Gregory P Harlow; Agnieszka Dudzik; Maciej Szaleniec; Shih-Yuan Liu; Johann Heider Journal: Angew Chem Int Ed Engl Date: 2013-01-28 Impact factor: 15.336
Authors: Jia-Sheng Lu; Soo-Byung Ko; Nicholas R Walters; Youngjin Kang; Francoise Sauriol; Suning Wang Journal: Angew Chem Int Ed Engl Date: 2013-04-05 Impact factor: 15.336
Authors: Jennifer E Thomson; Craig D Campbell; Carmen Concellón; Nicolas Duguet; Kathryn Rix; Alexandra M Z Slawin; Andrew D Smith Journal: J Org Chem Date: 2008-03-06 Impact factor: 4.354
Authors: Klara Edel; Sarah A Brough; Ashley N Lamm; Shih-Yuan Liu; Holger F Bettinger Journal: Angew Chem Int Ed Engl Date: 2015-06-11 Impact factor: 15.336
Authors: Klara Edel; Xinyu Yang; Jacob S A Ishibashi; Ashley N Lamm; Cäcilia Maichle-Mössmer; Zachary X Giustra; Shih-Yuan Liu; Holger F Bettinger Journal: Angew Chem Int Ed Engl Date: 2018-03-30 Impact factor: 15.336