Studies of Boron-Nitrogen Compounds. II. Preparation and Reactions of B-Trichloroborazole<sup>1</sup>

Brennan, Gerald Lee; Dahl, Gerd H.; Schaeffer, Riley

doi:10.1021/ja01509a011

Cited by 24 publications

(6 citation statements)

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“…The substitution is feasible with CN, SCN, ONO, ONO 2 , ClO 4 , and N 3 . [98][99][100] The silver salt of the nucleophile in dry acetonitrile is typically used for these metathesis reactions. However, the potassium salt of thiocyanate has also been used to obtain B-trithiocyanatoborazine.…”

Section: Synthesis Of B-trisubstituted Borazines By Substitution Reac...mentioning

confidence: 99%

“…However, the potassium salt of thiocyanate has also been used to obtain B-trithiocyanatoborazine. 98 An important reaction of B-trichloroborazine is the substitution with sodium alkoxides/sodium phenoxide in dry benzene. 101 Employing this method, B-trialkoxy-and Btriphenoxy-N-trimethylborazines 105 were prepared in 14-58% isolated yields from 19 (Scheme 53).…”

Section: Synthesis Of B-trisubstituted Borazines By Substitution Reac...mentioning

confidence: 99%

“…101 Similarly reaction with glacial acetic acid leads to formation of a degradation product and not the substituted borazine. 98 Step 1…”

Section: Synthesis Of B-trisubstituted Borazines By Substitution Reac...mentioning

confidence: 99%

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Synthesis and Reactions of Borazines

Neogi

Szpilman

2021

Synthesis

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Given the wide array of current applications of borazine-based materials, synthetic access to these compounds is of importance. This review summarizes the many ways of preparing borazines and its carbo-substituted analogues. In addition, the functionalization of borazines is covered. The synthesis of molecules incorporating more than one borazine units as well as aspects of unsymmetrically substituted borazines are not included. The literature has been covered comprehensively until the end of 2020.

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Section: Synthesis Of B-trisubstituted Borazines By Substitution Reac...mentioning

confidence: 99%

Section: Synthesis Of B-trisubstituted Borazines By Substitution Reac...mentioning

confidence: 99%

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Synthesis and Reactions of Borazines

Neogi

Szpilman

2021

Synthesis

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“…However, the title compound displays a near planar borazine ring, whereas (II) shows a boat conformation. For further synthetic details, see: Brennan et al (1960). Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: XSHELL.…”

Section: Related Literaturementioning

confidence: 99%

“…Compound (I) was obtained using a modification of the published procedure of Brennan, et al (1960). One equivalent of 2,4-Bis(dimethylamino)-6-chloro-1,3,5-trimethylborazine was reacted with one equivalent of silver nitrate in acetonitrile.…”

Section: S2 Experimentalmentioning

confidence: 99%

2,4-Bis(dimethylamino)-1,3,5-trimethyl-6-(nitrooxy)borazine

Rodriguez

Borek

2013

Acta Cryst E

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Key indicators: single-crystal X-ray study; T = 193 K; mean (O-B) = 0.004 Å; R factor = 0.046; wR factor = 0.124; data-to-parameter ratio = 14.1.In the title compound, C 7 H 21 B 3 N 6 O 3 , the r.m.s. deviation of the borazine ring atoms is 0.019 Å . The dimethylamino groups are orientated at 41.80 (7) and 36.43 (7) with respect to the borazine ring. The nitrooxy group is almost normal to the borazine ring [dihedral angle = 85.33 (14) ]. The methyl C atom trans to the NO 3 group is displaced by À0.512 (3) Å from the ring plane, whereas the two ortho-methyl C atoms are displaced by 0.239 (3) and 0.178 (3) Å . Related literature2,4-Bis(dimethylamino)-6-chloro-1,3,5-trimethylborazine (II) (Rodriguez & Borek, 2013) displays a similar structure to the title compound. However, the title compound displays a near planar borazine ring, whereas (II) shows a boat conformation. For further synthetic details, see: Brennan et al. (1960). ExperimentalCrystal data

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