2004
DOI: 10.1002/zaac.200400333
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1‐Azonia‐2‐boratanaphthalenes

Abstract: The 1‐azonia‐2‐boratanaphthalenes (NH)(BX)C8H6 can be synthesized from 2‐aminostyrene and the dihaloboranes XBHal2 (1‐4: X = Cl, Br, iPr, tBu). Further derivatives (NH)(BX)C8H6 are obtained from 1 by replacing Cl by alkoxy or alkyl groups [5‐8: X = OMe, OtBu, Me, (CH2)3NMe2]. The hydrolysis of 1 gives a mixture of the bis(azoniaboratanaphthyl) oxide [(NH)BC8H6]2O (9) and the hydroxy derivative (NH)[B(OH)]C8H6 (10). The diboryl oxide 9 crystallizes in the space group C2/c. The lithiation of 4 at the nitrogen at… Show more

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Cited by 66 publications
(62 citation statements)
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“…3,9 Paetzold synthesized 2,1-borazaronaphthalenes via a three component reaction employing aniline, an aryldichloroborane, and phenylacetylene (Scheme 1, IIA ). 10a As mentioned above, in early syntheses of N -substituted 2,1-borazaronaphthalenes, functionalization at nitrogen took place subsequent to ring formation in a second process under strongly basic reaction conditions. 8 However, Paetzold developed a different set of conditions for the synthesis of N -substituted 1,2-borazaronaphthalenes (Scheme 1, IIB ).…”
Section: Introductionmentioning
confidence: 98%
“…3,9 Paetzold synthesized 2,1-borazaronaphthalenes via a three component reaction employing aniline, an aryldichloroborane, and phenylacetylene (Scheme 1, IIA ). 10a As mentioned above, in early syntheses of N -substituted 2,1-borazaronaphthalenes, functionalization at nitrogen took place subsequent to ring formation in a second process under strongly basic reaction conditions. 8 However, Paetzold developed a different set of conditions for the synthesis of N -substituted 1,2-borazaronaphthalenes (Scheme 1, IIB ).…”
Section: Introductionmentioning
confidence: 98%
“…[8] Dewar and White pioneered the chemistry of monocyclic and ring-fused polycyclic 1,2-azaborine derivatives in the 1960s. [9] Recently, contributions by the groups of Ashe, [10] Piers, [11] and Paetzold, [12] as well as our group [13] have further advanced the preparation of novel BN heterocycles and sparked a renewed interest in the chemistry and properties of these compounds. [14] Despite the advances achieved to date, and given the powerful tools made available by modern chemical synthesis, it is surprising that a simple heterocycle such as the parent 1,2-dihydro-1,2-azaborine 1 has remained elusive.…”
mentioning
confidence: 98%
“…6 and 7). [15,16] The Piers group has focused on the formation of heterocyclic analogues of the PAHs carbazole, phenanthrene (8), and triphenylene (9).…”
mentioning
confidence: 99%