SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 46, Issue 36, 2007, Pages 6894-6898

The thermal retro[2+2+2]cycloaddition of cyclohexane activated by triscyclobutenannelation: Concerted all-disrotatory versus stepwise conrotatory pathways to fused [12]annulenes

(10) Eichberg, Michael J a Houk, K N b Lehmann, Jürg a Leonard, Philip W a Märker, Anne a Norton, Joseph E b Sawicka, Dorota b Vollhardt, K Peter C a Whitener, Glenn D a Wolff, Stefan a

a UNIVERSITY OF CALIFORNIA (United States)

b UNIVERSITY OF CALIFORNIA (United States)

Author keywords

Ab initio calculations; Cage compounds; Electrocyclic reactions; Isomerization; Strained molecules

Indexed keywords

BUTANE; COMPUTATION THEORY; CYCLOADDITION; ISOMERIZATION;

AB INITIO CALCULATIONS; CAGE COMPOUNDS; ELECTROCYCLIC REACTIONS; STRAINED MOLECULES;

CYCLOHEXANE;

EID: 34548781364 PISSN: 14337851 EISSN: None Source Type: Journal
DOI: 10.1002/anie.200702474 Document Type: Article

Times cited : (19)

References (50)

1
- 0345970701
- For a seemingly abortive effort, see
- a) For a seemingly abortive effort, see: C. Rücker, H. Müller-Bötticher, W.-D. Braschwitz, H. Prinzbach, U. Reifenstahl, H. Irngartinger, Liebigs Ann./Recueil 1997, 967;
- (1997) Liebigs Ann./Recueil , pp. 967
- Rücker, C.¹ Müller-Bötticher, H.² Braschwitz, W.-D.³ Prinzbach, H.⁴ Reifenstahl, U.⁵ Irngartinger, H.⁶

2
- 49549146383
- the trans- perfluoroderivative has been claimed: W. R. Hertler, J. Fluorine Chem. 1975, 6, 171.
- b) the trans- perfluoroderivative has been claimed: W. R. Hertler, J. Fluorine Chem. 1975, 6, 171.

3
- 33846191100
- For a review, see: A. de Meijere, S. I. Kozhushkov, H. Schill, Chem. Rev. 2006, 106, 4926; see also:
- a) For a review, see: A. de Meijere, S. I. Kozhushkov, H. Schill, Chem. Rev. 2006, 106, 4926; see also:

4
- 0347337794
- b) A. de Meijere, C.-H. Lee, B. Bengtson, E. Pohl, S. I. Kozhushkov, P. R. Schreiner, R. Boese, T. Haumann, Chem. Eur. J. 2003, 9, 5481;
- (2003) Chem. Eur. J , vol.9 , pp. 5481
- de Meijere, A.¹ Lee, C.-H.² Bengtson, B.³ Pohl, E.⁴ Kozhushkov, S.I.⁵ Schreiner, P.R.⁶ Boese, R.⁷ Haumann, T.⁸

5
- 0000396720
- c) D. Sawicka, K. N. Houk, J. Mol. Model. 2000, 6, 158;
- (2000) J. Mol. Model , vol.6 , pp. 158
- Sawicka, D.¹ Houk, K.N.²

6
- 0002892591
- d) D. Sawicka, K. N. Houk, J. Chem. Soc. Perkin Trans. 2 1999, 2349.
- (1999) J. Chem. Soc. Perkin Trans. 2 , pp. 2349
- Sawicka, D.¹ Houk, K.N.²

7
- 0043090706
- M. Maas, M. Lutterbeck, D. Hunkler, H. Prinzbach, Tetrahedron Lett. 1983, 24, 2143.
- (1983) Tetrahedron Lett , vol.24 , pp. 2143
- Maas, M.¹ Lutterbeck, M.² Hunkler, D.³ Prinzbach, H.⁴

8
- 33750155226
- A. Fattahi, L. Lis, Z. Tian, S. R. Kass, Angew. Chem. 2006, 118, 5106;
- (2006) Angew. Chem , vol.118 , pp. 5106
- Fattahi, A.¹ Lis, L.² Tian, Z.³ Kass, S.R.⁴

9
- 33746731720
- Angew. Chem. Int. Ed. 2006, 45, 4984.
- (2006) Chem. Int. Ed , vol.45 , pp. 4984
- Angew¹

10
- 0004266297
- Academic, New York
- a) J. J. Gajewski, Hydrocarbon Thermal Isomerizations, Academic, New York, 1981;
- (1981) Hydrocarbon Thermal Isomerizations
- Gajewski, J.J.¹

11
- 0037955548
- for a more recent discussion, see:b, and references therein
- for a more recent discussion, see:b) P. S. Lee, S. Sakai, P. Hörstermann, W. R. Roth, E. A. Kallel, K. N. Houk, J. Am. Chem. Soc. 2003, 125, 5839, and references therein.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 5839
- Lee, P.S.¹ Sakai, S.² Hörstermann, P.³ Roth, W.R.⁴ Kallel, E.A.⁵ Houk, K.N.⁶

12
- 33744763967
- 2055, and references therein;
- a) C. Silva López, O. N. Faza, Á. R. de Lera, Org. Lett. 2006, 8, 2055, and references therein;
- (2006) Org. Lett , vol.8
- Silva López, C.¹ Faza, O.N.² de Lera, A.R.³

13
- 34548788112
- the power of orbital-symmetry control is evident even in the aromatization of Dewar benzene:R. W. A. Havenith, L. W. Jenneskens, J. H. van Lenthe, J. Mol. Struct. (Theochem) 1999, 492, 111.
- b) the power of orbital-symmetry control is evident even in the aromatization of Dewar benzene:R. W. A. Havenith, L. W. Jenneskens, J. H. van Lenthe, J. Mol. Struct. (Theochem) 1999, 492, 111.

14
- 33750042917
- 4525, and references therein;
- a) S.-C. Chuang, F. R. Clemente, S. I. Khan, K. N. Houk, Y. Rubin, Org. Lett. 2006, 8, 4525, and references therein;
- (2006) Org. Lett , vol.8
- Chuang, S.-C.¹ Clemente, F.R.² Khan, S.I.³ Houk, K.N.⁴ Rubin, Y.⁵

15
- 0002619479
- b) Y. Rubin, Top. Curr. Chem. 1999, 199, 67.
- (1999) Top. Curr. Chem , vol.199 , pp. 67
- Rubin, Y.¹

16
- 33845411895
- a) H. Dodziuk, M. Ostrowski, Eur. J. Org. Chem. 2006, 5231,
- (2006) Eur. J. Org. Chem , pp. 5231
- Dodziuk, H.¹ Ostrowski, M.²

17
- 34548747228
- and references therein; b H. Dodziuk, Top. Stereochem. 1994, 21, 351.
- and references therein; b) H. Dodziuk, Top. Stereochem. 1994, 21, 351.

18
- 33846187214
- For a review, see
- For a review, see: E. L. Spitler, C. A. Johnson II, M. M. Haley, Chem. Rev. 2006, 106, 5344.
- (2006) Chem. Rev , vol.106 , pp. 5344
- Spitler, E.L.¹ Johnson II, C.A.² Haley, M.M.³

19
- 33751316996
- See, for example
- a) See, for example: A. Pla-Quintana, A. Torrent, A. Dachs, A. Roglans, R. Pleixats, M. Moreno-Mañas, T. Parella, J. Bene-Buchholz, Organometallics 2006, 25, 5612;
- (2006) Organometallics , vol.25 , pp. 5612
- Pla-Quintana, A.¹ Torrent, A.² Dachs, A.³ Roglans, A.⁴ Pleixats, R.⁵ Moreno-Mañas, M.⁶ Parella, T.⁷ Bene-Buchholz, J.⁸

20
- 0002726044
- review
- b) review: C. Moberg, Angew. Chem. 1998, 110, 260;
- (1998) Angew. Chem , vol.110 , pp. 260
- Moberg, C.¹

21
- 0032536470
- Angew. Chem. Int. Ed. 1998, 37, 248.
- (1998) Chem. Int. Ed , vol.37 , pp. 248
- Angew¹

22
- 0035938174
- a) Y. Kuwatani, T. Yoshida, A. Kusaka, M. Oda, K. Hara, M. Yoshida, H. Matsuyama, M. Iyoda, Tetrahedron 2001, 57, 3567;
- (2001) Tetrahedron , vol.57 , pp. 3567
- Kuwatani, Y.¹ Yoshida, T.² Kusaka, A.³ Oda, M.⁴ Hara, K.⁵ Yoshida, M.⁶ Matsuyama, H.⁷ Iyoda, M.⁸

23
- 0001735890
- b) D. L. Mohler, K. P. C. Vollhardt, S. Wolff, Angew. Chem. 1990, 102, 1200;
- (1990) Angew. Chem , vol.102 , pp. 1200
- Mohler, D.L.¹ Vollhardt, K.P.C.² Wolff, S.³

24
- 33749084191
- Angew. Chem. Int. Ed. Engl. 1990, 29, 1151.
- (1990) Angew. Chem. Int. Ed. Engl , vol.29 , pp. 1151

25
- 84989437622
- See also
- See also: R. Eckrich, D. Kuck, Synlett 1993, 344.
- (1993) Synlett , pp. 344
- Eckrich, R.¹ Kuck, D.²

26
- 34548791503
- All new compounds gave satisfactory analytical and spectral data (see Experimental Section and Supporting Information, Hydrocarbons 2-4, 6a, and 8a-c were subjected to X-ray crystallographic analysis. 2: C24H30, crystal size 0.34 x 0.21 x 0.12 mm3, space group Pnma, scan range 3.0 < 2θ < 50.9°, T= 158(2) K, a, 9.7048(19, b, 16.116(3, c, 11.813(2) Å, α, 90.00, β, 90.00, γ, 90.00°, V, 1847.5(6) Å3, Z, 4, ρcalcd, 1.145 g cm-3, μ(MoKα, 0.64 cm-1, 1666 unique reflections, of which 1044 were taken as observed [I > 2σI, R, 0.0688, Rw, 0.2024. 3: C24H26, crystal size 0.27 x 0.17 x 0.15 mm3, space group Pnma, scan range 3.0 < 2θ < 51.1°, T, 15
- w = 0.1108. CCDC 648165-CCDC 648171 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

27
- 34548784692
- A series of isodesmic and homodesmotic reactions indicates that the relative strain energy increases slightly in the order 2→5. For example, the homodesmotic equation 5+ cyclohexene →4+ benzene and its analogues yielding 3 and 2, starting from 4 and 3, respectively, gives strain, 0, 2.0, 4.7, and 8.5 kcal mol -1 along the series see Supporting Information
- -1 along the series (see Supporting Information).

28
- 34548744940
- The triple Birch-reduction product 6a behaves as 2 and converts quantitatively into the hexadehydro analogue of 8a at 130°C (see Supporting Information).
- The triple Birch-reduction product 6a behaves as 2 and converts quantitatively into the hexadehydro analogue of 8a at 130°C (see Supporting Information).

29
- 0030921160
- P. Mendes, Trends Biochem. Sci. 1997, 22, 361.
- (1997) Trends Biochem. Sci , vol.22 , pp. 361
- Mendes, P.¹

30
- 0000949188
- For model systems, see
- For model systems, see: H. A. Staab, F. Graf, K. Doerner, A. Nissen, Chem. Ber. 1971, 104, 1159.
- (1971) Chem. Ber , vol.104 , pp. 1159
- Staab, H.A.¹ Graf, F.² Doerner, K.³ Nissen, A.⁴

31
- 34548793235
- ≠ = 1.8(2.0), within error bars of our current data;
- ≠ = 1.8(2.0), within error bars of our current data;

32
- 27744489233
- for an appraisal of the performance of various methods in the estimation of activation barriers and structures, see, for example b D. H. Ess, K. N. Houk, J. Phys. Chem. A 2005, 109, 9542, and references therein;
- for an appraisal of the performance of various methods in the estimation of activation barriers and structures, see, for example b) D. H. Ess, K. N. Houk, J. Phys. Chem. A 2005, 109, 9542, and references therein;

33
- 0035807658
- c) R. A. Pascal, Jr., J. Phys. Chem. A 2001, 105, 9040.
- (2001) J. Phys. Chem. A , vol.105 , pp. 9040
- Pascal Jr., R.A.¹

34
- 34548769588
- The observed trends in activation barriers follow the relative energies of the products formed after the rate-determining transition states (see Supporting Information);
- a) The observed trends in activation barriers follow the relative energies of the products formed after the rate-determining transition states (see Supporting Information);

35
- 34548790435
- At the suggestion of a referee, we have calculated the data in Table 1 also at the B3PW91/6-31Gc level of theory, revealing the same trends and crossover in mechanism
- b) At the suggestion of a referee, we have calculated the data in Table 1 also at the B3PW91/6-31Gc) level of theory, revealing the same trends and "crossover" in mechanism.

36
- 34547808174
- a) J. F. M. Oth, H. Röttele, G. Schröder, Tetrahedron Lett. 1970, 11, 61;
- (1970) Tetrahedron Lett , vol.11 , pp. 61
- Oth, J.F.M.¹ Röttele, H.² Schröder, G.³

37
- 17744377437
- b) C. Castro, W. L. Karney, C. M. H. Vu, S. E. Burkhardt, M. A. Valencia, J. Org. Chem. 2005, 70, 3602.
- (2005) J. Org. Chem , vol.70 , pp. 3602
- Castro, C.¹ Karney, W.L.² Vu, C.M.H.³ Burkhardt, S.E.⁴ Valencia, M.A.⁵

38
- 22144476163
- C. Castro, W. L. Karney, M. A. Valencia, C. M. H. Vu, R. P. Pemberton, J. Am. Chem. Soc. 2005, 127, 9704.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 9704
- Castro, C.¹ Karney, W.L.² Valencia, M.A.³ Vu, C.M.H.⁴ Pemberton, R.P.⁵

39
- 34548780575
- This isomer emerges initially as the unsymmetrical rotamer. Fast trans-double-bond rotation in [12]annulene is well established, see refs, 20, 21
- This isomer emerges initially as the unsymmetrical rotamer. Fast trans-double-bond rotation in [12]annulene is well established, see refs. [20, 21].

40
- 34548792642
- This transformation was proposed to proceed by direct [2+2+2, homo-Diels-Alder) cycloaddition. However, transition states for such one-step connections between 10 and 8 could not be located computationally. Instead, 6π closure (ΔH≠= 24.1 kcal mol -1 from 10d) was found to give syn-11d (ΔH≠, 3.5 kcal mol-1, which continues on to 8d Scheme 3
- -1), which continues on to 8d (Scheme 3).

41
- 0035185215
- a)T. Yoshida, Y. Kuwatani, K. Hara, M. Yoshida, H. Matsuyama, M. Iyoda, S. Nagase, Tetrahedron Lett. 2001, 42, 53;
- (2001) Tetrahedron Lett , vol.42 , pp. 53
- Yoshida, T.¹ Kuwatani, Y.² Hara, K.³ Yoshida, M.⁴ Matsuyama, H.⁵ Iyoda, M.⁶ Nagase, S.⁷

42
- 2142698640
- b) M. D. Banciu, I. Simion, A. Banciu, A. Petride, C. Draghici, Rev. Roum. Chim. 1991, 36, 1101;
- (1991) Rev. Roum. Chim , vol.36 , pp. 1101
- Banciu, M.D.¹ Simion, I.² Banciu, A.³ Petride, A.⁴ Draghici, C.⁵

43
- 0000948769
- c) M. W. Tausch, M. Elian, A. Bucur, E. Ciorãnescu, Chem. Ber. 1977, 110, 1744;
- (1977) Chem. Ber , vol.110 , pp. 1744
- Tausch, M.W.¹ Elian, M.² Bucur, A.³ Ciorãnescu, E.⁴

44
- 0007729925
- d) H. Irngartinger, Chem. Ber. 1975, 108, 1017.
- (1975) Chem. Ber , vol.108 , pp. 1017
- Irngartinger, H.¹

45
- 34548751516
- For experimental data on the conformational mobility of related bisbenzocyclooctatrienes, see: a
- For experimental data on the conformational mobility of related bisbenzocyclooctatrienes, see: a) H. Meier, H. Gugel, M. Barth, U. Plücken, Z. Naturforsch. B 1980, 35, 477
- (1980) Z. Naturforsch. B , vol.35 , pp. 477
- Meier, H.¹ Gugel, H.² Barth, M.³ Plücken, U.⁴

46
- 0040743320
- b) T. S. Cantell, J. V. Silverton, J. Org. Chem. 1979, 44, 4477.
- (1979) J. Org. Chem , vol.44 , pp. 4477
- Cantell, T.S.¹ Silverton, J.V.²

47
- 3042993534
- For the 6π-ring closures of 1,2-diethenylcyclohexenes, see a
- For the 6π-ring closures of 1,2-diethenylcyclohexenes, see a) E. N. Marvell, C. Hilton, M. Cleary, J. Org. Chem. 1983, 48, 4272;
- (1983) J. Org. Chem , vol.48 , pp. 4272
- Marvell, E.N.¹ Hilton, C.² Cleary, M.³

48
- 0001534374
- b) E. N. Marvell, G. Caple, C. Delphey, J. Platt, N. Polston, J. Tashiro, Tetrahedron 1973, 29, 3797.
- (1973) Tetrahedron , vol.29 , pp. 3797
- Marvell, E.N.¹ Caple, G.² Delphey, C.³ Platt, J.⁴ Polston, N.⁵ Tashiro, J.⁶

49
- 0043027666
- C. Castro, C. M. Isborn, W. L. Karney, M. Mauksch, P. v. R. Schleyer, Org. Lett. 2002, 4, 3431.
- (2002) Org. Lett , vol.4 , pp. 3431
- Castro, C.¹ Isborn, C.M.² Karney, W.L.³ Mauksch, M.⁴ Schleyer, P.V.R.⁵

50
- 34548780016
- Gaussian 03 (Revision C.02): M. J. Frisch et al., see Supporting Information.
- Gaussian 03 (Revision C.02): M. J. Frisch et al., see Supporting Information.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.