SCOPUS 정보 검색 플랫폼

Organometallics

Volumn 27, Issue 3, 2008, Pages 320-323

Synthesis, structure, and facile ring flipping of a bicyclo[1.1.0] tetrasilane

(3) Ueba Ohshima, Kiyomi a Iwamoto, Takeaki a Kira, Mitsuo a

a TOHOKU UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ISOMERIZATION; SYNTHESIS (CHEMICAL);

AIR-SENSITIVE YELLOW CRYSTALS; ALTERNATIVE SYNTHETIC ROUTE;

AROMATIC COMPOUNDS;

EID: 39649090980 PISSN: 02767333 EISSN: None Source Type: Journal
DOI: 10.1021/om7011375 Document Type: Article

Times cited : (32)

References (51)

1
- 39649123093
- For reviews on bicyclo[1.1.0]butanes, see: (a) wiberg, K. B. Adv. Alicycl. Chem. 1968, 2, 185.
- For reviews on bicyclo[1.1.0]butanes, see: (a) wiberg, K. B. Adv. Alicycl. Chem. 1968, 2, 185.

2
- 0004258370
- Rappoport, Z. Ed, Wiley: New York
- (b) Hoz, S. In The Chemistry of the Cyclopropyl Group; Rappoport, Z. Ed.; Wiley: New York, 1987; p 1121.
- (1987) The Chemistry of the Cyclopropyl Group , pp. 1121
- Hoz, S.¹

3
- 0037374010
- (c) Hall, H. K., Jr.; Padia, A. B. J. Polym. Sci., Part A 2003, 41, 625.
- (2003) J. Polym. Sci., Part A , vol.41 , pp. 625
- Hall Jr., H.K.¹ Padia, A.B.²

4
- 33748240837
- For reviews on cyclic silanes, see: a
- For reviews on cyclic silanes, see: (a) Tsumuraya, T.; Batcheller, S. A.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1991, 30, 902.
- (1991) Angew. Chem., Int. Ed. Engl , vol.30 , pp. 902
- Tsumuraya, T.¹ Batcheller, S.A.² Masamune, S.³

5
- 0000393538
- (b) Hengge, E.; Janoschek, R. Chem. Rev. 1995, 95, 1495.
- (1995) Chem. Rev , vol.95 , pp. 1495
- Hengge, E.¹ Janoschek, R.²

6
- 33748880663
- (c) Driess, M.; Grützmacher, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 828.
- (1996) Angew. Chem., Int. Ed. Engl , vol.35 , pp. 828
- Driess, M.¹ Grützmacher, H.²

7
- 0003670973
- Rappoport, Z, Apeloig, Y, Eds, Wiley: New York, Chapter 3
- (d) Sekiguchi, A.; Nagase, S. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; Wiley: New York, 1998; Vol. 2,Chapter 3.
- (1998) The Chemistry of Organic Silicon Compounds , vol.2
- Sekiguchi, A.¹ Nagase, S.²

8
- 0032842555
- (e) Weidenbruch, M. Eur. J. Inorg. Chem. 1999, 373.
- (1999) Eur. J. Inorg. Chem , pp. 373
- Weidenbruch, M.¹

9
- 4243940423
- For reviews on bond stretch isomerism, see: a
- For reviews on bond stretch isomerism, see: (a) Parkin, G. Chem. Rev. 1993, 93, 887.
- (1993) Chem. Rev , vol.93 , pp. 887
- Parkin, G.¹

10
- 0037021045
- (b) Grützmacher, H.; Breher, F. Angew. Chem., Int. Ed. 2002, 41, 4006.
- (2002) Angew. Chem., Int. Ed , vol.41 , pp. 4006
- Grützmacher, H.¹ Breher, F.²

11
- 33846871028
- (c) Breher, F. Coord. Chem. Rev. 2007, 251, 1007.
- (2007) Coord. Chem. Rev , vol.251 , pp. 1007
- Breher, F.¹

12
- 39649093708
- For concepts of bond stretch isomerism, see: a
- For concepts of bond stretch isomerism, see: (a) Stohrer, W.-D.; Hoffmann, R. J. Am. Chem. Soc. 1972, 94, 119.
- (1972) J. Am. Chem. Soc , vol.94 , pp. 119
- Stohrer, W.-D.¹ Hoffmann, R.²

13
- 0000308917
- (b) Stohrer, W.-D.; Hoffmann, R. J. Am. Chem. Soc. 1972, 94, 1661.
- (1972) J. Am. Chem. Soc , vol.94 , pp. 1661
- Stohrer, W.-D.¹ Hoffmann, R.²

14
- 37049070247
- (a) Dabisch, T.; Schoeller, W. W. J. Chem. Soc., Chem. Commun. 1986, 896.
- (1986) J. Chem. Soc., Chem. Commun , pp. 896
- Dabisch, T.¹ Schoeller, W.W.²

15
- 84985527640
- (b) Schleyer, P. v. R.; Sax, A. F.; Kalcher, J.; Janoschek, R. Angew. Chem., Int. Ed. Engl. 1987, 26, 364.
- (1987) Angew. Chem., Int. Ed. Engl , vol.26 , pp. 364
- Schleyer, P.V.R.¹ Sax, A.F.² Kalcher, J.³ Janoschek, R.⁴

16
- 33845281409
- (c) Schoeller, W. W.; Dabisch, T.; Busch, T. Inorg. Chem. 1987, 26, 4383.
- (1987) Inorg. Chem , vol.26 , pp. 4383
- Schoeller, W.W.¹ Dabisch, T.² Busch, T.³

17
- 37049075201
- (d) Nagase, S.; Kudo, T. J. Chem. Soc., Chem. Commun. 1988, 54.
- (1988) J. Chem. Soc., Chem. Commun , pp. 54
- Nagase, S.¹ Kudo, T.²

18
- 33845278514
- (e) Boatz, J. A.; Gordon, M. S. J. Phys. Chem. 1988, 92, 3037.
- (1988) J. Phys. Chem , vol.92 , pp. 3037
- Boatz, J.A.¹ Gordon, M.S.²

19
- 0007657218
- (f) Boatz, J. A.; Gordon, M. S. J. Phys. Chem. 1989, 93, 2888.
- (1989) J. Phys. Chem , vol.93 , pp. 2888
- Boatz, J.A.¹ Gordon, M.S.²

20
- 0025031821
- (g) Kitchen, D.; Jackson, J. E.; Allen, L. C. J. Am. Chem. Soc. 1990, 112, 3408.
- (1990) J. Am. Chem. Soc , vol.112 , pp. 3408
- Kitchen, D.¹ Jackson, J.E.² Allen, L.C.³

21
- 0009457074
- (h) Boatz, J. A.; Gordon, M. S. Organometallics 1996, 15, 2118.
- (1996) Organometallics , vol.15 , pp. 2118
- Boatz, J.A.¹ Gordon, M.S.²

22
- 4143052378
- (i) Koch, R.; Bruhn, T.; Weidenbruch, M. J. Mol. Struct. (THEOCHEM) 2004, 680, 91.
- (2004) J. Mol. Struct. (THEOCHEM) , vol.680 , pp. 91
- Koch, R.¹ Bruhn, T.² Weidenbruch, M.³

23
- 33845378984
- (a) Masamune, S.; Kabe, Y.; Collins, S. J. Am. Chem. Soc. 1985, 107, 5552.
- (1985) J. Am. Chem. Soc , vol.107 , pp. 5552
- Masamune, S.¹ Kabe, Y.² Collins, S.³

24
- 84985611060
- (b) Jones, R.; Williams, D. J.; Kabe, Y.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1986, 25, 173.
- (1986) Angew. Chem., Int. Ed. Engl , vol.25 , pp. 173
- Jones, R.¹ Williams, D.J.² Kabe, Y.³ Masamune, S.⁴

25
- 0001361938
- Wiberg, N.; Auer, H.; Wagner, S.; Polborn, K.; Kramer, G. J. Organomet. Chem. 2001, 619, 110.
- (2001) J. Organomet. Chem , vol.619 , pp. 110
- Wiberg, N.¹ Auer, H.² Wagner, S.³ Polborn, K.⁴ Kramer, G.⁵

26
- 0035915322
- Iwamoto, T.; Yin, D.; Kabuto, C.; Kira, M. J. Am. Chem. Soc. 2001, 123, 12730.
- (2001) J. Am. Chem. Soc , vol.123 , pp. 12730
- Iwamoto, T.¹ Yin, D.² Kabuto, C.³ Kira, M.⁴

27
- 84987224746
- (a) Fritz, G.; Wartanessian, S.; Matern, E.; Hönle, W.; von Schnering, H. G. Z. Anorg. Allg. Chem. 1981, 475, 87.
- (1981) Z. Anorg. Allg. Chem , vol.475 , pp. 87
- Fritz, G.¹ Wartanessian, S.² Matern, E.³ Hönle, W.⁴ von Schnering, H.G.⁵

28
- 0006896034
- (b) Fritz, G.; Thomas, J. J. Organomet. Chem. 1984, 271, 107.
- (1984) J. Organomet. Chem , vol.271 , pp. 107
- Fritz, G.¹ Thomas, J.²

29
- 33847652881
- Lee, V. Y.; Yasuda, H.; Sekiguchi, A. J. Am. Chem. Soc. 2007, 129, 2436.
- (2007) J. Am. Chem. Soc , vol.129 , pp. 2436
- Lee, V.Y.¹ Yasuda, H.² Sekiguchi, A.³

30
- 0030994283
- For stable compounds including the silabicyclo[1.1.0]tetrasilane moiety, see: (a) Ando, W.; Shiba, T.; Hidaka, T.; Morihashi, K.; Kikuchi, O. J. Am. Chem. Soc. 1997, 119, 3629.
- For stable compounds including the silabicyclo[1.1.0]tetrasilane moiety, see: (a) Ando, W.; Shiba, T.; Hidaka, T.; Morihashi, K.; Kikuchi, O. J. Am. Chem. Soc. 1997, 119, 3629.

31
- 0032476811
- (b) Wiberg, N.; Auer, H.; Nöth, H.; Knizek, J.; Polborn, K. Angew. Chem., Int. Ed. 1998, 37, 2869.
- (1998) Angew. Chem., Int. Ed , vol.37 , pp. 2869
- Wiberg, N.¹ Auer, H.² Nöth, H.³ Knizek, J.⁴ Polborn, K.⁵

32
- 0033245443
- (c) Ichinohe, M.; Takahashi, N.; Sekiguchi, A. Chem. Lett. 1999, 553.
- (1999) Chem. Lett , pp. 553
- Ichinohe, M.¹ Takahashi, N.² Sekiguchi, A.³

33
- 18844461266
- (d) Scheschkewitz, D. Angew. Chem., Int. Ed. 2005, 44, 2954.
- (2005) Angew. Chem., Int. Ed , vol.44 , pp. 2954
- Scheschkewitz, D.¹

34
- 0029906740
- (a) Kira, M.; Iwamoto, T.; Kabuto, C. J. Am. Chem. Soc. 1996, 118, 10303.
- (1996) J. Am. Chem. Soc , vol.118 , pp. 10303
- Kira, M.¹ Iwamoto, T.² Kabuto, C.³

35
- 39649125479
- (b) Iwamoto, T.; Kira, M. Chem. Lett. 1998, 227.
- (1998) Chem. Lett , pp. 227
- Iwamoto, T.¹ Kira, M.²

36
- 0037586577
- (c) Iwamoto, T.; Tamura, M.; Kabuto, C.; Kira, M. Organometallics 2003, 22, 2342.
- (2003) Organometallics , vol.22 , pp. 2342
- Iwamoto, T.¹ Tamura, M.² Kabuto, C.³ Kira, M.⁴

37
- 39649105950
- 14 with lithium followed by 1,2-dibromoethane. Details of the preparation of 3 and 6 are shown in the Supporting Information.
- 14 with lithium followed by 1,2-dibromoethane. Details of the preparation of 3 and 6 are shown in the Supporting Information.

38
- 0036010457
- Kira, M.; Iwamoto, T.; Maruyama, T.; Kuzuguchi, T.; Yin, D.; Kabuto, C.; Sakurai, H. Dalton Trans. 2002, 1539.
- (2002) Dalton Trans , pp. 1539
- Kira, M.¹ Iwamoto, T.² Maruyama, T.³ Kuzuguchi, T.⁴ Yin, D.⁵ Kabuto, C.⁶ Sakurai, H.⁷

39
- 39649091024
- 3: air-sensitive yellow crystals; mp <0 °C dec; 1H NMR (400 MHz, toluene-d8, 243 K, δ) 0.44 (s, 12H, Si-Me, 0.46 (s, 24H, Si-Me, 1.20 (s, 54H, t-Bu, 1H NMR (400 MHz, toluene-d8, 208 K, δ) 0.44 (s, 12H, Si-Me, 0.48 (s, 12H, Si-Me, 0.50 (s, 12H, Si-Me, 1.23 (s, 54H, t-Bu, 13C NMR (100 MHz, THF-d8, 208 K, δ, 0.9, 3.4 (br, 17.9 (br, 19.8 (br, 20.5, 27.6, 28.8, 30.1; 29Si NMR (79.5 MHz, toluene-d8, 208 K, δ, 145.1 (S(SiMe2-t-Bu, 90.6 (Si(SiMe2-t-Bu) 2, 3.7 (br, Si(AMe2-Z-Bu)2, 8.1 (br, Si(SiMe2-t-Bu)2, 8.7 (Si(SiMe2-t-Bu, UV-vis (3-methylpentane, 230 K) λmax (ε/103) 299 (16.6, 390 (2.6, 459 1.3, Anal. Calcd for C36H 90Si10: C, 53.78; H, 11.28. Found: C, 53.68; H, 11.19. The UV-vis spectra of
- 10: C, 53.78; H, 11.28. Found: C, 53.68; H, 11.19. The UV-vis spectra of 3 are remarkably temperature dependent between 110 and 230 K, with an isosbestic point at 395 nm (see Figure S1 in the Supporting Information).

40
- 39649112228
- 3, R1 = 7.2%, wR2 = 13.5%, GOF = 1.32.
- 3, R1 = 7.2%, wR2 = 13.5%, GOF = 1.32.

41
- 39649107393
- 5
- 5

42
- 0013497730
- (a) Pomerantz, M.; Abrahamson, E. W. J. Am. Chem. Soc. 1966, 88, 3970.
- (1966) J. Am. Chem. Soc , vol.88 , pp. 3970
- Pomerantz, M.¹ Abrahamson, E.W.²

43
- 0038700408
- (b) Schulman, J. M.; Fisanick, G. J. J. Am. Chem. Soc. 1970, 92, 6653.
- (1970) J. Am. Chem. Soc , vol.92 , pp. 6653
- Schulman, J.M.¹ Fisanick, G.J.²

44
- 0030572325
- (c) Inagaki, S.; Kakefu, T.; Yamamoto, T.; Wasada, H. J. Phys. Chem. 1996, 100, 9615.
- (1996) J. Phys. Chem , vol.100 , pp. 9615
- Inagaki, S.¹ Kakefu, T.² Yamamoto, T.³ Wasada, H.⁴

45
- 39649115467
- Although in previous several theoretical papers5a-h both LB and SB structures have been located as local minima for 7, recent calculations for 7 at higher theoretical levels show no energy minimum at the SB structure.5h,i
- 5h,i

46
- 39649106720
- 1H NMR spectra of 3 was performed using the gNMR program package: Peter, H. M.; gNMR V4.1.0; Cherwell Scientific: Oxford, U.K., 1999.
- 1H NMR spectra of 3 was performed using the gNMR program package: Peter, H. M.; gNMR V4.1.0; Cherwell Scientific: Oxford, U.K., 1999.

47
- 39649090353
- For the Eyring plot, see the Supporting Information
- For the Eyring plot, see the Supporting Information.

48
- 33845281819
- Collins, S, Durler, R, Rauk, A. J. Am. Chem. Soc. 1987, 109, 2564; 1987, 109, 6217, correction, While Collins et al. have estimated the energy difference between the short-bond structure and planar transition state as the ring-flipping barrier, Gordon et al. have found a ring-flipping pathway connecting short-bond and long-bond isomers of 1,3-disubstituted bicyclotetrasilanes (1,3-R2H4Si 4 (R, H, Me, t-Bu, The energy difference between the short-bond isomer and the transition state of the ring flipping is dependent on the level of theory: 7.9 kcal mol-1 at the GVB/6-31G(d)//GVB/3-21G* level and 17.5 kcal mo-l at the MP2/6-31G(d)//GVB/3-21G* level for the parent bicyclotetrasilane (7).5h
- 5h

49
- 0037040584
- 22 See also for related main-group-element analogues of planar cyclobutane-1,3-diyl: Scheschkewitz, D.; Amii, H.; Gornitzka, H.; Schoeller, W. W.; Bourissou, D.; Bertrand, G. Science 2002, 295, 1880.
- 22 See also for related main-group-element analogues of planar cyclobutane-1,3-diyl: Scheschkewitz, D.; Amii, H.; Gornitzka, H.; Schoeller, W. W.; Bourissou, D.; Bertrand, G. Science 2002, 295, 1880.

50
- 0042531956
- Schoeller, W. W.; Rozhenko, A.; Bourissou, D.; Bertrand, G. Chem. Eur. J. 2003, 9, 3611.
- (2003) Chem. Eur. J , vol.9 , pp. 3611
- Schoeller, W.W.¹ Rozhenko, A.² Bourissou, D.³ Bertrand, G.⁴

51
- 85022314079
- Sakurai, H. Ed, CMC: Tokyo
- Kabe, Y. In Synthesis and Application of Organosilicon Polymer; Sakurai, H. Ed.; CMC: Tokyo, 1989; p 75.
- (1989) Synthesis and Application of Organosilicon Polymer , pp. 75
- Kabe, Y.¹

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.