Abstract
The kinetic stabilization using sterically demanding bulky substituents or ligands provides us an exciting opportunity to explore a large variety of organoelement unsaturated compounds. We recently demonstrated that a new class of fused-ring bulky octa-R-substituted s-hydrindacenyl groups (Rind groups) can act as unique protecting groups in the main group chemistry as well as in the transition metal chemistry. This manuscript describes the recent advances in the chemistry of π-conjugated systems containing sp2-hybridized silicon atoms stabilized by the bulky Rind groups. The synthesis and characterization of various π-conjugated disilene compounds as well as a planar rhombic charge-separated tetrasilacyclobutadiene incorporating the bulky Rind groups are covered.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
West R, Fink MJ, Michl J (1981) Science 214:1343
For reviews: (a) Okazaki R, West R (1996) Adv Organomet Chem 39:231. (b) Power PP (1999) Chem Rev 99:3463. (c) Kira M, Iwamoto T (2006) Adv Organomet Chem 54:73. (d) Wang Y, Robinson GH (2009) Chem Commun 5201. (e) Fischer RC, Power PP (2010) Chem Rev 110:4877. (f) Lee YV, Sekiguchi A (2010) Organometallic compounds of low-coordinate Si, Ge, Sn and Pb. Wiley, Chichester (g) Scheschkewitz D (2011) Chem Lett 40:2 (h) Asay M, Sekiguchi A (2012) Bull Chem Soc Jpn 85:1245. (i) Sasamori T, Tokitoh N, Bull Chem Soc Jpn 86:1005
Wakita K, Tokitoh N, Okazaki R, Nagase S (2000) Angew Chem Int Ed 39:634
Ishida S, Iwamoto T, Kabuto C, Kira M (2003) Nature 421:725
Sekiguchi A, Kinjo R, Ichinohe M (2004) Science 305:1755
Suzuki K, Matsuo T, Hashizume D, Fueno H, Tanaka K, Tamao K (2011) Science 331:1306
Abersfelder K, White AJP, Rzepa HS, Scheschkewitz D (2010) Science 327:564
Wang Y, Xie Y, Wei P, King RB, Schaefer III HF, Schleyer PVR, Robinson GH (2008) Science 321:1069
Matsuo T, Suzuki K, Fukawa T, Li B, Ito M, Shoji Y, Otani T, Li L, Kobayashi M, Hachiya M, Tahara Y, Hashizume D, Fukunaga T, Fukazawa A, Li Y, Tsuji H, Tamao K (2011) Bull Chem Soc Jpn 84:1178
(a) Gates DP (2005) Top Curr Chem 250:107. (b) Baumgartner T, Réau R (2006) Chem Rev 106:4681. (c) Scheschkewitz D (2009) Chem Eur J 15:2476. (d) Matsuo T, Li B, Tamao K (2010) C R Chemie 13:1104. (e) Bates JI, Dugal-Tessier J, Gates DP, Dalton Trans 39:3151. (f) Matsuo T, Kobayashi M, Tamao K (2010) Dalton Trans 39:9203. (g) Simpson MC, Protasiewicz JD (2013) Pure Appl Chem 85:801
Bejan I, Scheschkewitz D (2007) Angew Chem Int Edn 46:5783. (b) Fukazawa A, Li Y, Yamaguchi S, Tsuji H, Tamao K (2007) J Am Chem Soc 129:14164
(a) Kobayashi M, Matsuo T, Fukunaga T, Hashizume D, Fueno H, Tanaka K, Tamao K (2010) J Am Chem Soc 132:15162. (b) Kobayashi M, Hayakawa N, Nakabayashi K, Matsuo T, Hashizume D, FuenoH, Tanaka K, Tamao K (2014) Chem Lett 43:432
Watanabe H, Takeuchi K, Fukawa N, Kato M, Goto M, Nagai Y (1987) Chem Lett 16:1341
Tamao K, Kobayashi M, Matsuo T, Furukawa S, Tsuji H (2012) Chem Commun 48:1030
(a) Bally T, Masamune S (1980) Tetrahedron 36:343. (b) Maier G Angew Chem Int Edn Engl 27:309. (c) Bally T (2006) Angew Chem Int Edn 45:6616
(a) Kimling H, Krebs A Angew Chem Int Edn Engl 11:932. (b) Irngartinger H, Rodewald H (1974) Angew Chem Int Edn Engl 13:740. (c) Delbaere LTJ, James MNG, Nakamura N, Masamune S (1975) J Am Chem Soc 97:1973. (d) Maier G, Pfriem S, Schäfer U, Matusch R (1978) Angew Chem Int Edn Engl 17:520. (e) Petersson EJ, Fanuele JC, Nimlos MR, Lemal DM, Ellison GB, Radziszewski JG (1997) J Am Chem Soc 119:11122. (f) Wu JI, Evangelista FA, Schleyer PR (2010) Org Lett 12:768. (g) Legrand Y-M, van der Lee A, Barboiu M (2010) Science 329:299
Bonačić-Koutecký V, Koutecký J, Michl J (1987) Angew Chem Int Ed Engl 26:170
Yates BF, Clabo DA Jr, Schaefer HF III (1988) Chem Phys Lett 143:421
(a) Wiberg N, Finger CMM, Polborn K (1993) Angew Chem Int Edn Engl 32:1054. (b) Ichinohe M, Toyoshima M, Kinjo R, Sekiguchi A (2003) J Am Chem Soc 125:13328
(a) Takanashi K, Lee VY, Matsuno T, Ichinohe M, Sekiguchi A (2005) J Am Chem Soc 127:5768. (b) Lee VY, Takanashi K, Matsuno T, Ichinohe M, Sekiguchi A (2004) J Am Chem Soc 126:4758
Chen Z, Wannere CS, Corminboeuf C, Puchta R, Schleyer PVR (2005) Chem Rev 105:3842
Tsurusaki A, Iizuka C, Otsuka K, Kyushin S (2013) J Am Chem Soc 135:16340
Szilvási T, Veszprémi T (2012) Organometallics 31:3207
Acknowledgment
The author thanks the Ministry of Education, Culture, Sports, Science, and Technology of Japan for the Grant-in-Aid for Specially Promoted Research (No. 19002008) and Scientific Research (B) (Nos. 24350031 and 15H03788). This work was also partially supported by MEXT-Supported Program for the Strategic Research Foundation at Private Universities 2014–2018, subsidy from MEXT and Kindai University. The calculations and experiments discussed in this article have been performed with many collaborators, whose names appear in the references. The author wishes to express his thanks to all of them for their kind collaboration, in particular, Prof. Kohei Tamao, for his continuous discussions.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2015 Springer Japan
About this chapter
Cite this chapter
Matsuo, T. (2015). π-Conjugated Disilenes and Tetrasilacyclobutadiene. In: Akasaka, T., Osuka, A., Fukuzumi, S., Kandori, H., Aso, Y. (eds) Chemical Science of π-Electron Systems. Springer, Tokyo. https://doi.org/10.1007/978-4-431-55357-1_23
Download citation
DOI: https://doi.org/10.1007/978-4-431-55357-1_23
Publisher Name: Springer, Tokyo
Print ISBN: 978-4-431-55356-4
Online ISBN: 978-4-431-55357-1
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)