Benzazole-N(SINGLE BOND)BH3 adducts. Reductive transposition of 2-benzimidazole, 2-benzothiazole, and 2-benzoxazole N(SINGLE BOND)BH3 adducts to 1,3,2-benzimidazaborole, 1,3,2-benzoxaborole, and 1,3,2-benzothiazaborole

  1. Itzia I. Padilla-Martínez1,*,
  2. Noemí Andrade-López2,
  3. Miguel Gama-Goicochea2,
  4. Eréndira Aguilar-Cruz2,
  5. Alejandro Cruz2,
  6. Rosalinda Contreras2,
  7. Hugo Tlahuext3

Article first published online: 7 DEC 1998

DOI: 10.1002/(SICI)1098-1071(199610)7:5<323::AID-HC7>3.0.CO;2-C

Issue

Heteroatom Chemistry

Heteroatom Chemistry

Volume 7, Issue 5, pages 323–335, 1996

Additional Information

How to Cite

Padilla-Martínez, I. I., Andrade-López, N., Gama-Goicochea, M., Aguilar-Cruz, E., Cruz, A., Contreras, R. and Tlahuext, H. (1996), Benzazole-N(SINGLE BOND)BH3 adducts. Reductive transposition of 2-benzimidazole, 2-benzothiazole, and 2-benzoxazole N(SINGLE BOND)BH3 adducts to 1,3,2-benzimidazaborole, 1,3,2-benzoxaborole, and 1,3,2-benzothiazaborole. Heteroatom Chem., 7: 323–335. doi: 10.1002/(SICI)1098-1071(199610)7:5<323::AID-HC7>3.0.CO;2-C

Author Information

  1. 1

    Departamento de Química, Unidad Profesional Interdisciplinaria de Biotecnología del IPN, Av. Acueducto s/n Barrio La Laguna Ticomán, México D. F. 07340, México

  2. 2

    Departamento de Química, Centro de Investigación y de Estudios Avanzados del IPN, Apartado Postal 14-740, México D.F. 07000, México

  3. 3

    Facultad de Ciencias, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Col. Chamilpa. Cuernavaca Morelos, México

*Departamento de Química, Unidad Profesional Interdisciplinaria de Biotecnología del IPN, Av. Acueducto s/n Barrio La Laguna Ticomán, México D. F. 07340, México

Publication History

  1. Issue published online: 7 DEC 1998
  2. Article first published online: 7 DEC 1998
  3. Manuscript Accepted: 29 APR 1996
  4. Manuscript Received: 25 MAR 1996

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Abstract

1,3,2-Benzimidazaborole, 1,3,2-benzoxaborole, and 1,3,2-benzothiazaborole were synthesized from the corresponding 2-benzazole N(SINGLE BOND)BH3 and 2-benzazole S(SINGLE BOND)BH3 adducts through a reductive transposition from the isolobal fragment X(SINGLE BOND)C(sp2) (DOUBLE BOND) N(sp2) (SINGLE BOND) B(sp3) (X (DOUBLE BOND) N, O, S) to the fragment X(SINGLE BOND)B(sp2) (DOUBLE BOND) N(sp2) (SINGLE BOND) C(sp3). N(SINGLE BOND)BH3 substitution shifts to lower frequencies 4-H, C-3a, and C-7a resonances. The X-ray diffraction analysis of 2-(o-methoxyphenyl)benzothiazole N(SINGLE BOND)BH3 adduct is reported. Two new tetracyclic boron-bridged compounds were observed as by-products (6,9-(ethyl)-diaza-2-oxa-1-bora[3,4,7,8]-dibenzobycyclo[4.3.0]-nona-3,7-diene, 6d, and 8-aza-9-oxa-2-thia-1-bora-[3,4,7,8]dibenzobycyclo[3.4.0]nona-3,7-diene, 15d, when 2-(o-methoxyphenyl)-1-ethylbenzimidazole-BH36b and 2-(o-methoxyphenyl)-benzothiazole-BH315b adducts were heated. © 1996 John Wiley & Sons, Inc.

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