메뉴 건너뛰기




Volumn 73, Issue 1, 2008, Pages 81-87

3-(Dimethylboryl)pyridine: Synthesis, structure, and remarkable steric effects in scrambling reactions

Author keywords

[No Author keywords available]

Indexed keywords

BOND LENGTHS; SCRAMBLING REACTIONS; STERIC EFFECTS;

EID: 37549014477     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7018043     Document Type: Article
Times cited : (10)

References (31)
  • 17
    • 37549058584 scopus 로고    scopus 로고
    • The price and boiling point of trimethylborane is U.S. $1080.00/10 g and -20°C, respectively. In addition, this reagent is not commercially available in Japan because it is a high-pressure gas.
    • The price and boiling point of trimethylborane is U.S. $1080.00/10 g and -20°C, respectively. In addition, this reagent is not commercially available in Japan because it is a high-pressure gas.
  • 20
    • 0001079081 scopus 로고    scopus 로고
    • Takeuchi, M.; Kijima, H.; Hamachi, I.; Shinkai, S. Bull. Chem. Soc. Jpn. 1997, 70, 699. In this paper and in private communications, Takeuchi et al. described the synthesis of 4, involving the hydrolysis of 2a (ref 4a) followed by esterification in 19% yield.
    • Takeuchi, M.; Kijima, H.; Hamachi, I.; Shinkai, S. Bull. Chem. Soc. Jpn. 1997, 70, 699. In this paper and in private communications, Takeuchi et al. described the synthesis of 4, involving the hydrolysis of 2a (ref 4a) followed by esterification in 19% yield.
  • 21
    • 37549002287 scopus 로고    scopus 로고
    • On the basis of the procedure reported by Ogawa et al. (J. Am. Chem. Soc. 1996, 118, 5783)
    • On the basis of the procedure reported by Ogawa et al. (J. Am. Chem. Soc. 1996, 118, 5783)
  • 22
    • 0037039899 scopus 로고    scopus 로고
    • and Wong et al. (J. Org. Chem. 2002, 67, 1041), which does not involve the production of boronic acid, we attempted the synthesis by reacting the lithiate of 3-pyridyl with trimethylborate, followed by removal of solvent and treatment with methanol. Unfortunately, polymeric materials were obtained.
    • and Wong et al. (J. Org. Chem. 2002, 67, 1041), which does not involve the production of boronic acid, we attempted the synthesis by reacting the lithiate of 3-pyridyl with trimethylborate, followed by removal of solvent and treatment with methanol. Unfortunately, polymeric materials were obtained.
  • 26
    • 37549047373 scopus 로고    scopus 로고
    • Since single crystals of 3 could not be obtained, the molecular structure was calculated by AM1. The THC value of the boron atom and the length of the B-N bond in 3a are estimated to average 80.8% and 1.634 Å, respectively.
    • Since single crystals of 3 could not be obtained, the molecular structure was calculated by AM1. The THC value of the boron atom and the length of the B-N bond in 3a are estimated to average 80.8% and 1.634 Å, respectively.
  • 27
    • 37549071647 scopus 로고    scopus 로고
    • Using AM1 calculations, we also estimated the enthalpic contribution to the free energy change associated with self-assembly: 1a, 11.2 kcal/mol; 2a, 10.9 kcal/mol; 3a, 9.2 kcal/mol. This order is not consistent with the scrambling conditions, nor does it support sole unimolecular dissociation of the B-N bond during scrambling
    • Using AM1 calculations, we also estimated the enthalpic contribution to the free energy change associated with self-assembly: 1a, 11.2 kcal/mol; 2a, 10.9 kcal/mol; 3a, 9.2 kcal/mol. This order is not consistent with the scrambling conditions, nor does it support sole unimolecular dissociation of the B-N bond during scrambling.
  • 28
    • 37549030321 scopus 로고    scopus 로고
    • As model compounds for monomer, we also used pyridine, 4-methylpyridine, or 4-methoxypyridine. However, standing at ambient temperature for several days remained unchanged.
    • As model compounds for monomer, we also used pyridine, 4-methylpyridine, or 4-methoxypyridine. However, standing at ambient temperature for several days remained unchanged.
  • 30
    • 2542495781 scopus 로고    scopus 로고
    • Moss, R. A, Platz, M. S, Jones, M, Jr, Eds, John Wiley & Sons, Inc, Hoboken, NJ
    • (b) Amyes, T. L.; Toteva, M. M.; Richard, J. P. In Reactive Intermediate Chemistry; Moss, R. A., Platz, M. S., Jones, M., Jr., Eds.; John Wiley & Sons, Inc.: Hoboken, NJ, 2004; p 41.
    • (2004) Reactive Intermediate Chemistry , pp. 41
    • Amyes, T.L.1    Toteva, M.M.2    Richard, J.P.3
  • 31
    • 0000356059 scopus 로고    scopus 로고
    • For the calculations of the complex of borane with aldehyde, THF, and ammonia, etc, see: DiMare, M. J. Org. Chem. 1996, 61, 8378. Also see ref 1h
    • For the calculations of the complex of borane with aldehyde, THF, and ammonia, etc., see: DiMare, M. J. Org. Chem. 1996, 61, 8378. Also see ref 1h.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.