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Skeletal isomerism within 1,3-disilabicyclo[1.1.0]butane and 2,3-disilabuta-1,3-diene derivatives

Takeaki Iwamoto 1
Takeaki Iwamoto
, 
Akifumi Kobayashi 1
Akifumi Kobayashi
, 
Naohiko Akasaka 1
Naohiko Akasaka
, 
Shintaro Ishida 1
Shintaro Ishida
10.1016/j.mencom.2022.01.012
Published 2022-01-03
Communication , Volume 32, Issue 1, 39-41
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Iwamoto T. et al. Skeletal isomerism within 1,3-disilabicyclo[1.1.0]butane and 2,3-disilabuta-1,3-diene derivatives // Mendeleev Communications. 2022. Vol. 32. No. 1. pp. 39-41.
GOST all authors (up to 50) Copy
Iwamoto T., Kobayashi A., Akasaka N., Ishida S. Skeletal isomerism within 1,3-disilabicyclo[1.1.0]butane and 2,3-disilabuta-1,3-diene derivatives // Mendeleev Communications. 2022. Vol. 32. No. 1. pp. 39-41.
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TY - JOUR
DO - 10.1016/j.mencom.2022.01.012
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.01.012
TI - Skeletal isomerism within 1,3-disilabicyclo[1.1.0]butane and 2,3-disilabuta-1,3-diene derivatives
T2 - Mendeleev Communications
AU - Iwamoto, Takeaki
AU - Kobayashi, Akifumi
AU - Akasaka, Naohiko
AU - Ishida, Shintaro
PY - 2022
DA - 2022/01/03
PB - Mendeleev Communications
SP - 39-41
IS - 1
VL - 32
ER -
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@article{2022_Iwamoto,
author = {Takeaki Iwamoto and Akifumi Kobayashi and Naohiko Akasaka and Shintaro Ishida},
title = {Skeletal isomerism within 1,3-disilabicyclo[1.1.0]butane and 2,3-disilabuta-1,3-diene derivatives},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Jan},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.01.012},
number = {1},
pages = {39--41},
doi = {10.1016/j.mencom.2022.01.012}
}
MLA
Cite this
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Iwamoto, Takeaki, et al. “Skeletal isomerism within 1,3-disilabicyclo[1.1.0]butane and 2,3-disilabuta-1,3-diene derivatives.” Mendeleev Communications, vol. 32, no. 1, Jan. 2022, pp. 39-41. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.01.012.

Keywords

1,3-Disilabicyclo[1.1.0]butanes
2,3-Disilabuta-1,3-dienes
Bicyclo[1.1.0]butanes
organosilicon compounds
Skeletal isomerization
Tetrasilanes

Abstract

A bis-adamantane-spiro-fused 1,3-bis(triisopropylsilyl)-1,3-disilabicyclo[1.1.0]butane equilibrates with the corresponding 2,3-bis(triisopropylsilyl)-1,3-disilabuta-1,3-diene with a ratio of 1:19. The 1,3-disilabuta-1,3-diene was fully characterized by a combination of multinuclear NMR and UV-VIS spectroscopies, elemental analysis, and single-crystal X-ray diffraction analysis.

References

1.
10.1016/j.mencom.2022.01.012_b0005
Woodward
The Conservation of Orbital Symmetry, 1970
4.
Isomerization Of Bicyclo[1.1.0]butane to Butadiene
Nguyen K.A., Gordon M.S.
Journal of the American Chemical Society, 1995
5.
Orbital Symmetry and the Photochemical Ring Opening of Cyclobutene
Leigh W.J., Postigo J.A., Venneri P.C.
Journal of the American Chemical Society, 1995
7.
10.1016/j.mencom.2022.01.012_b0035
Müller
Organosilicon Chemistry IV, 2000
8.
Theoretical Study of Thermal Isomerization of Silacyclobutene to Cyclopropene
Shiota Y., Yasunaga M., Naka A., Ishikawa M., Yoshizawa K.
Organometallics, 2004
9.
Valence isomerization of 2-phospha-4-silabicyclo[1.1.0]butane: a high-level ab initio study
Slootweg J.C., Ehlers A.W., Lammertsma K.
Journal of Molecular Modeling, 2006
10.
Theoretical group 14 chemistry. Part 2. Si4R6: a theoretical approach
Koch R., Bruhn T., Weidenbruch M.
Journal of Molecular Structure THEOCHEM, 2004
12.
The First Stable Cyclic Disilene:  Hexakis(trialkylsilyl)tetrasilacyclobutene
Kira M., Iwamoto T., Kabuto C.
Journal of the American Chemical Society, 1996
14.
Crystal Structure of a Stable Silabenzene and Its Photochemical Valence Isomerization into the Corresponding Silabenzvalene
Wakita K., Tokitoh N., Okazaki R., Takagi N., Nagase S.
Journal of the American Chemical Society, 2000
17.
1,2,5,6-Tetrasilabenzobenzvalene: A Valence Isomer of 1,2,3,4-Tetrasilanaphthalene
Takanashi K., Lee V.Y., Ichinohe M., Sekiguchi A.
Chemistry Letters, 2007
18.
Isomeric Metamorphosis:  Si3E (E = S, Se, and Te) Bicyclo[1.1.0]butane and Cyclobutene
Lee V.Y., Miyazaki S., Yasuda H., Sekiguchi A.
Journal of the American Chemical Society, 2008
20.
From a Si3-Cyclopropene to a Si3S-Bicyclo[1.1.0]butane to a Si3S-Cyclopropene to a Si3S2-Bicyclo[1.1.0]butane: Back-and-Forth, and In-Between
Lee V.Y., Gapurenko O.A., Miyazaki S., Sekiguchi A., Minyaev R.M., Minkin V.I., Gornitzka H.
Angewandte Chemie - International Edition, 2015
21.
Reactivity of a Peraryl Cyclotrisilene (c -Si3 R 4 ) Toward Chalcogens
Zhao H., Klemmer L., Cowley M.J., Huch V., Zimmer M., Scheschkewitz D.
Zeitschrift fur Anorganische und Allgemeine Chemie, 2018
22.
Photochemical isomerization of 1-sila-2,4-cyclohexadienes
Nakadaira Y., Kanouchi S., Sakurai H.
Journal of the American Chemical Society, 1974
23.
Silacyclobutenes: a simple synthesis
Block E., Revelle L.K.
Journal of the American Chemical Society, 1978
26.
1,5-Silyl migrations as a route to acyclic 1-sila-1,3-butadienes
Barton T.J., Wulff W.D., Burns S.A.
Organometallics, 1983
28.
Silacyclobutadienes: generation of 1-mesityl-2,3,4-tri-tert-butyl-1-silacyclobutadiene
Fink M.J., Puranik D.B., Johnson M.P.
Journal of the American Chemical Society, 1988
29.
Gas phase reactions of 1,1-dimethylsilabutadiene
Conlin R.T., Namavari M.
Journal of Organometallic Chemistry, 1989
31.
The rate of ring closure of 1,1-dimethyl-2-phenyl-1-silabuta-1,3-diene to 1,1-dimethyl-2-phenyl-1-silacyclobutene
Conlin R.T., Zhang S., Namavari M., Bobbitt K.L., Fink M.J.
Organometallics, 1989
32.
Synthesis, Structure, Photoluminescence and Photoreactivity of 2,3‐Diphenyl‐4‐neopentyl‐1‐silacyclobut‐2‐enes
Yan D., Thomson M., Backer M., Bolte M., Hahn R., Berger R., Fann W., Roskos H., Auner N.
Chemistry - A European Journal, 2009
33.
Isolable 2,3-Disila-1,3-butadiene from a Double Sila-Peterson Reaction
Motomatsu D., Ishida S., Ohno K., Iwamoto T.
Chemistry - A European Journal, 2014
34.
The First 1,3-Disilabicyclo[1.1.0]butane with Long-Bridge Silicon−Silicon Bond
Iwamoto T., Yin D., Kabuto C., Kira M.
Journal of the American Chemical Society, 2001
35.
Lithiated 1,3-Disilabicyclo[1.1.0]butanes Synthesized via Selective Cleavage of Exocyclic Si–Si Bonds on Bridgehead Silicon Atoms
Iwamoto T., Yin D., Kobayashi A., Tamura M., Motomatsu D., Akasaka N., Yokouchi Y., Ishida S., Kira M.
Organometallics, 2021
36.
Silabutadienes. Internal Rotations and π-Conjugation. A Density Functional Theory Study
Xi H., Karni M., Apeloig Y.
Journal of Physical Chemistry A, 2008
37.
Novel Stable Silenes via a Sila-Peterson-type Reaction. Molecular Structure and Reactivity
Apeloig Y., Bendikov M., Yuzefovich M., Nakash M., Bravo-Zhivotovskii D., Bläser D., Boese R.
Journal of the American Chemical Society, 1996
38.
10.1016/j.mencom.2022.01.012_b0190
Sheldrick
SADABS, 1996
39.
Crystal structure refinement withSHELXL
Sheldrick G.M.
Acta crystallographica. Section C, Structural chemistry, 2015
40.
(a) K. Wakita, Yadokari-XG: Software for Crystal Structure Analyses, 2001
41.
KABUTO C., AKINE S., NEMOTO T., KWON E.
Nihon Kessho Gakkaishi, 2009