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Volumn 9, Issue 11, 2003, Pages 2419-2438

Preparation, structure, and unique thermal [2 + 2], [4 + 2], and [3 + 2] cycloaddition reactions of 4-vinylideneoxazolidin-2-one

Author keywords

Alkenes; Alkynes; Allenes; Cycloaddition; Dienes

Indexed keywords

ADDITION REACTIONS; CHEMICAL BONDS; OLEFINS; PARAFFINS;

EID: 0038000454     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200304586     Document Type: Article
Times cited : (57)

References (160)
  • 20
    • 0034623558 scopus 로고    scopus 로고
    • Transition-metal catalyzed [2 + 2] cyclodimerization of allenes: a) S. Saito, K. Hirayama, C. Kabuto, Y. Yamamoto, J. Am. Chem. Soc. 2000, 122, 10776-10780; b) K. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49-92.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 10776-10780
    • Saito, S.1    Hirayama, K.2    Kabuto, C.3    Yamamoto, Y.4
  • 21
    • 0002110351 scopus 로고    scopus 로고
    • Transition-metal catalyzed [2 + 2] cyclodimerization of allenes: a) S. Saito, K. Hirayama, C. Kabuto, Y. Yamamoto, J. Am. Chem. Soc. 2000, 122, 10776-10780; b) K. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49-92.
    • (1996) Chem. Rev. , vol.96 , pp. 49-92
    • Lautens, K.1    Klute, W.2    Tam, W.3
  • 22
    • 0011955699 scopus 로고
    • Transition-metal catalyzed [2 + 2] cycloaddition of allenes and alkenes: M. Murakami, H. Amii, K. Itami, Y. Ito, Angew. Chem. 1995, 107, 1649-1650; Angew. Chem. Int. Ed. Engl. 1995, 34, 1476-1477.
    • (1995) Angew. Chem. , vol.107 , pp. 1649-1650
    • Murakami, M.1    Amii, H.2    Itami, K.3    Ito, Y.4
  • 23
    • 33748222868 scopus 로고
    • Transition-metal catalyzed [2 + 2] cycloaddition of allenes and alkenes: M. Murakami, H. Amii, K. Itami, Y. Ito, Angew. Chem. 1995, 107, 1649-1650; Angew. Chem. Int. Ed. Engl. 1995, 34, 1476-1477.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 1476-1477
  • 38
    • 0000675615 scopus 로고
    • intramolecular version
    • m) H. R. Seikaly, T. T. Tidwell, Tetrahedron 1986, 42, 2587-2613; intramolecular version;
    • (1986) Tetrahedron , vol.42 , pp. 2587-2613
    • Seikaly, H.R.1    Tidwell, T.T.2
  • 41
    • 0033578661 scopus 로고    scopus 로고
    • o) J.-M. Adam, L. Ghosez, K. N. Houk, Angew. Chem. 1999, 111, 2897-2899; Angew. Chem. Int. Ed. Engl. 1999, 38, 2728-2730;
    • (1999) Angew. Chem. Int. Ed. Engl. , vol.38 , pp. 2728-2730
  • 57
    • 0037791232 scopus 로고
    • and references therein
    • c) D. J. Pasto, K. D. Sugi, J. Org. Chem. 1991, 56, 6216-6224 and references therein;
    • (1991) J. Org. Chem. , vol.56 , pp. 6216-6224
    • Pasto, D.J.1    Sugi, K.D.2
  • 58
  • 60
    • 0032500072 scopus 로고    scopus 로고
    • 2-Methylenecyclobutene formation via thermal radical cyclization of ω-enyne-allene: a) C. Ikemoto, T. Kawano, I. Ueda, Tetrahedron Lett. 1998, 39, 5053-5056; b) M. Schmittel, S. Kiau, T. Siebert, M. Strittmatter, Tetrahedron Lett. 1996, 37, 7691-7694; c) J. G. Garcia, B. Ramos, L. M. Pratt, A. Rodriguez, Tetrahedron Lett. 1995, 36, 7391-7394; d) T. Gillmann, T. Hülsen, W. Massa, S. Wocadlo, Synlett 1995, 1257-1259; e) K. Fujiwara, H. Sakai, M. Hirama, J. Org. Chem. 1991, 56, 1688-1689.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 5053-5056
    • Ikemoto, C.1    Kawano, T.2    Ueda, I.3
  • 61
    • 0030597031 scopus 로고    scopus 로고
    • 2-Methylenecyclobutene formation via thermal radical cyclization of ω-enyne-allene: a) C. Ikemoto, T. Kawano, I. Ueda, Tetrahedron Lett. 1998, 39, 5053-5056; b) M. Schmittel, S. Kiau, T. Siebert, M. Strittmatter, Tetrahedron Lett. 1996, 37, 7691-7694; c) J. G. Garcia, B. Ramos, L. M. Pratt, A. Rodriguez, Tetrahedron Lett. 1995, 36, 7391-7394; d) T. Gillmann, T. Hülsen, W. Massa, S. Wocadlo, Synlett 1995, 1257-1259; e) K. Fujiwara, H. Sakai, M. Hirama, J. Org. Chem. 1991, 56, 1688-1689.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7691-7694
    • Schmittel, M.1    Kiau, S.2    Siebert, T.3    Strittmatter, M.4
  • 62
    • 0029134096 scopus 로고
    • 2-Methylenecyclobutene formation via thermal radical cyclization of ω-enyne-allene: a) C. Ikemoto, T. Kawano, I. Ueda, Tetrahedron Lett. 1998, 39, 5053-5056; b) M. Schmittel, S. Kiau, T. Siebert, M. Strittmatter, Tetrahedron Lett. 1996, 37, 7691-7694; c) J. G. Garcia, B. Ramos, L. M. Pratt, A. Rodriguez, Tetrahedron Lett. 1995, 36, 7391-7394; d) T. Gillmann, T. Hülsen, W. Massa, S. Wocadlo, Synlett 1995, 1257-1259; e) K. Fujiwara, H. Sakai, M. Hirama, J. Org. Chem. 1991, 56, 1688-1689.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 7391-7394
    • Garcia, J.G.1    Ramos, B.2    Pratt, L.M.3    Rodriguez, A.4
  • 63
    • 77954853973 scopus 로고
    • 2-Methylenecyclobutene formation via thermal radical cyclization of ω-enyne-allene: a) C. Ikemoto, T. Kawano, I. Ueda, Tetrahedron Lett. 1998, 39, 5053-5056; b) M. Schmittel, S. Kiau, T. Siebert, M. Strittmatter, Tetrahedron Lett. 1996, 37, 7691-7694; c) J. G. Garcia, B. Ramos, L. M. Pratt, A. Rodriguez, Tetrahedron Lett. 1995, 36, 7391-7394; d) T. Gillmann, T. Hülsen, W. Massa, S. Wocadlo, Synlett 1995, 1257-1259; e) K. Fujiwara, H. Sakai, M. Hirama, J. Org. Chem. 1991, 56, 1688-1689.
    • (1995) Synlett , pp. 1257-1259
    • Gillmann, T.1    Hülsen, T.2    Massa, W.3    Wocadlo, S.4
  • 64
    • 0001096101 scopus 로고
    • 2-Methylenecyclobutene formation via thermal radical cyclization of ω-enyne-allene: a) C. Ikemoto, T. Kawano, I. Ueda, Tetrahedron Lett. 1998, 39, 5053-5056; b) M. Schmittel, S. Kiau, T. Siebert, M. Strittmatter, Tetrahedron Lett. 1996, 37, 7691-7694; c) J. G. Garcia, B. Ramos, L. M. Pratt, A. Rodriguez, Tetrahedron Lett. 1995, 36, 7391-7394; d) T. Gillmann, T. Hülsen, W. Massa, S. Wocadlo, Synlett 1995, 1257-1259; e) K. Fujiwara, H. Sakai, M. Hirama, J. Org. Chem. 1991, 56, 1688-1689.
    • (1991) J. Org. Chem. , vol.56 , pp. 1688-1689
    • Fujiwara, K.1    Sakai, H.2    Hirama, M.3
  • 67
    • 0037791231 scopus 로고    scopus 로고
    • Allenes with bent bond of bond angles within 161-176° due to ring strain, torsional strain, and/or packing effects in the crystals: a) F. Hojo, K. Fujiki, W. Ando, Organometallics 1996, 15, 3606-3610;
    • (1996) Organometallics , vol.15 , pp. 3606-3610
    • Hojo, F.1    Fujiki, K.2    Ando, W.3
  • 72
    • 33845183891 scopus 로고
    • f) R. P. Johnson, Chem. Rev. 1989, 89, 1111-1124; g) M. Traetteberg, P. Bakken, A. Almenningen, J. Mol. Struct. 1981, 70, 287-295;
    • (1989) Chem. Rev. , vol.89 , pp. 1111-1124
    • Johnson, R.P.1
  • 74
    • 4243853993 scopus 로고
    • allenes with bent bond due to coordination to transition-metals
    • h) V. A. Gieren, C. Hahn, Acta Crystallogr. 1979, B35, 1008-1010; allenes with bent bond due to coordination to transition-metals;
    • (1979) Acta Crystallogr. , vol.B35 , pp. 1008-1010
    • Gieren, V.A.1    Hahn, C.2
  • 76
    • 0038574111 scopus 로고
    • allenes with bent bond stabilized by coordination to transition metals
    • j) C. E. Kerr, B. E. Eaton, J. A. Kaduk, Organometallics 1995, 14, 269-273; allenes with bent bond stabilized by coordination to transition metals;
    • (1995) Organometallics , vol.14 , pp. 269-273
    • Kerr, C.E.1    Eaton, B.E.2    Kaduk, J.A.3
  • 80
    • 0035896195 scopus 로고    scopus 로고
    • matrix-isolated cyclohepta-1,2,4.6-tetraene
    • n) R. Warmuth, M. A. Marvel, Chem. Eur. J. 2001, 7, 1209-1220; matrix-isolated cyclohepta-1,2,4.6-tetraene;
    • (2001) Chem. Eur. J. , vol.7 , pp. 1209-1220
    • Warmuth, R.1    Marvel, M.A.2
  • 85
    • 0037791245 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of this compound is compiled in the Supporting Information.
  • 86
    • 0037791246 scopus 로고    scopus 로고
    • note
    • CCDC-181558 (2a),-181724 (2b),-188289 (2g),-181726 (2k),181555(2m),-181553(2n),-181554(2p),-181559(2q),-181551(7c), -181560 (8a),-179982 (8k) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; (fax: (+44) 1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk).
  • 88
    • 0000649003 scopus 로고    scopus 로고
    • Ketenes are such unstable molecules that a vast number of X-ray crystallographic analyses have been reported as their transition-metal complexes. X-ray structural analyses of ketenes without coordination of transition metals; a) L. Pandolfo, G. Paiaro, L. K. Dragani, C. Maccatom, R. Bertani, G. Facchin, L. Zanotto, P. Ganis, G. Valle, Organometallics 1996, 15, 3250-3252; b) N. S. Radu, M. P. Engeler, C. P. Gerlach. T. D. Tilley, J. Am. Chem. Soc. 1995, 117, 3621-3622; c) C. O. Kappe, R. A. Evans, C. H. L. Kennard, C. Wentrup, J. Am. Chem. Soc. 1991, 113, 4233-4237; d) J. J. Daly, J. Chem. Soc. A 1967, 1913-1917.
    • (1996) Organometallics , vol.15 , pp. 3250-3252
    • Pandolfo, L.1    Paiaro, G.2    Dragani, L.K.3    Maccatom, C.4    Bertani, R.5    Facchin, G.6    Zanotto, L.7    Ganis, P.8    Valle, G.9
  • 89
    • 0000366801 scopus 로고
    • Ketenes are such unstable molecules that a vast number of X-ray crystallographic analyses have been reported as their transition-metal complexes. X-ray structural analyses of ketenes without coordination of transition metals; a) L. Pandolfo, G. Paiaro, L. K. Dragani, C. Maccatom, R. Bertani, G. Facchin, L. Zanotto, P. Ganis, G. Valle, Organometallics 1996, 15, 3250-3252; b) N. S. Radu, M. P. Engeler, C. P. Gerlach. T. D. Tilley, J. Am. Chem. Soc. 1995, 117, 3621-3622; c) C. O. Kappe, R. A. Evans, C. H. L. Kennard, C. Wentrup, J. Am. Chem. Soc. 1991, 113, 4233-4237; d) J. J. Daly, J. Chem. Soc. A 1967, 1913-1917.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 3621-3622
    • Radu, N.S.1    Engeler, M.P.2    Gerlach, C.P.3    Tilley, T.D.4
  • 90
    • 0001346928 scopus 로고
    • Ketenes are such unstable molecules that a vast number of X-ray crystallographic analyses have been reported as their transition-metal complexes. X-ray structural analyses of ketenes without coordination of transition metals; a) L. Pandolfo, G. Paiaro, L. K. Dragani, C. Maccatom, R. Bertani, G. Facchin, L. Zanotto, P. Ganis, G. Valle, Organometallics 1996, 15, 3250-3252; b) N. S. Radu, M. P. Engeler, C. P. Gerlach. T. D. Tilley, J. Am. Chem. Soc. 1995, 117, 3621-3622; c) C. O. Kappe, R. A. Evans, C. H. L. Kennard, C. Wentrup, J. Am. Chem. Soc. 1991, 113, 4233-4237; d) J. J. Daly, J. Chem. Soc. A 1967, 1913-1917.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 4233-4237
    • Kappe, C.O.1    Evans, R.A.2    Kennard, C.H.L.3    Wentrup, C.4
  • 91
    • 37049138715 scopus 로고
    • Ketenes are such unstable molecules that a vast number of X-ray crystallographic analyses have been reported as their transition-metal complexes. X-ray structural analyses of ketenes without coordination of transition metals; a) L. Pandolfo, G. Paiaro, L. K. Dragani, C. Maccatom, R. Bertani, G. Facchin, L. Zanotto, P. Ganis, G. Valle, Organometallics 1996, 15, 3250-3252; b) N. S. Radu, M. P. Engeler, C. P. Gerlach. T. D. Tilley, J. Am. Chem. Soc. 1995, 117, 3621-3622; c) C. O. Kappe, R. A. Evans, C. H. L. Kennard, C. Wentrup, J. Am. Chem. Soc. 1991, 113, 4233-4237; d) J. J. Daly, J. Chem. Soc. A 1967, 1913-1917.
    • (1967) J. Chem. Soc. A , pp. 1913-1917
    • Daly, J.J.1
  • 92
    • 0038467858 scopus 로고    scopus 로고
    • note
    • The NMR spectrum is given in the Supporting Information.
  • 94
    • 0033555653 scopus 로고    scopus 로고
    • Y. Horino, M. Kimura, Y. Wakamiya, T. Okajima, Y. Tamaru, Angew. Chem. 1999, 111, 123-126, Angew. Chem. Int. Ed. 1999, 38, 121-123
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 121-123
  • 96
    • 84984170869 scopus 로고
    • Complete loss of stereochemical integrity of cis-β-monodeuteriostyrene for the [2 + 2] addition with cyclohexa-1,3-diene: a) M. Christl, M. Schreck, Chem. Ber. 1987, 120, 915-920; b) S. Harnos, S. Tivakornpannarai, E. E. Waali, Tetrahedron Lett. 1986, 27, 3701-3704.
    • (1987) Chem. Ber. , vol.120 , pp. 915-920
    • Christl, M.1    Schreck, M.2
  • 97
    • 0038128904 scopus 로고
    • Complete loss of stereochemical integrity of cis-β-monodeuteriostyrene for the [2 + 2] addition with cyclohexa-1,3-diene: a) M. Christl, M. Schreck, Chem. Ber. 1987, 120, 915-920; b) S. Harnos, S. Tivakornpannarai, E. E. Waali, Tetrahedron Lett. 1986, 27, 3701-3704.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 3701-3704
    • Harnos, S.1    Tivakornpannarai, S.2    Waali, E.E.3
  • 112
    • 0000171233 scopus 로고    scopus 로고
    • Transition-metal catalyzed Diels-Alder reaction of allene/diene; a) M. Murakami, K. Itami, Y. Ito, J. Am. Chem. Soc. 1997, 119, 7163-7164; b) P. A. Wender, T. E. Jenkins, S. Suzuki, J. Am. Chem. Soc. 1995, 117, 1843-1844.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 7163-7164
    • Murakami, M.1    Itami, K.2    Ito, Y.3
  • 113
    • 0000551283 scopus 로고
    • Transition-metal catalyzed Diels-Alder reaction of allene/diene; a) M. Murakami, K. Itami, Y. Ito, J. Am. Chem. Soc. 1997, 119, 7163-7164; b) P. A. Wender, T. E. Jenkins, S. Suzuki, J. Am. Chem. Soc. 1995, 117, 1843-1844.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 1843-1844
    • Wender, P.A.1    Jenkins, T.E.2    Suzuki, S.3
  • 116
    • 0031708442 scopus 로고    scopus 로고
    • b) M. Murakami, M. Ubukata, K. Itami, Y. Ito, Angew, Chem. 1998, 110, 2362-2364; Angew. Chem. Int. Ed. 1998, 37, 2248-2250:;
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 2248-2250
  • 118
    • 0033553143 scopus 로고    scopus 로고
    • Concomitant [2 + 2] and [4 + 2] addition reactions for the reaction of allenes and dienes: a) M. E. Jung, N. Nishimura, J. Am. Chem. Soc. 1999, 121, 3529-3530; b) J. R. Bull, N. S. Desmond-Smith, S. J. Heggie, R. Hunter. F.-C. Tien, Synlett 1998, 900-902; c) M. E. Jung, J. A. Lowe III, M. A. Lyster, M. Node, R. W. Pfluger, R. W. Brown, Tetrahedron 1984, 40, 4751-4766; see also, ref. [6] and [8a,b].
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 3529-3530
    • Jung, M.E.1    Nishimura, N.2
  • 119
    • 0002409301 scopus 로고    scopus 로고
    • Concomitant [2 + 2] and [4 + 2] addition reactions for the reaction of allenes and dienes: a) M. E. Jung, N. Nishimura, J. Am. Chem. Soc. 1999, 121, 3529-3530; b) J. R. Bull, N. S. Desmond-Smith, S. J. Heggie, R. Hunter. F.-C. Tien, Synlett 1998, 900-902; c) M. E. Jung, J. A. Lowe III, M. A. Lyster, M. Node, R. W. Pfluger, R. W. Brown, Tetrahedron 1984, 40, 4751-4766; see also, ref. [6] and [8a,b].
    • (1998) Synlett , pp. 900-902
    • Bull, J.R.1    Desmond-Smith, N.S.2    Heggie, S.J.3    Hunter, R.4    Tien, F.-C.5
  • 120
    • 0021750591 scopus 로고
    • see also, ref. [6] and [8a,b]
    • Concomitant [2 + 2] and [4 + 2] addition reactions for the reaction of allenes and dienes: a) M. E. Jung, N. Nishimura, J. Am. Chem. Soc. 1999, 121, 3529-3530; b) J. R. Bull, N. S. Desmond-Smith, S. J. Heggie, R. Hunter. F.-C. Tien, Synlett 1998, 900-902; c) M. E. Jung, J. A. Lowe III, M. A. Lyster, M. Node, R. W. Pfluger, R. W. Brown, Tetrahedron 1984, 40, 4751-4766; see also, ref. [6] and [8a,b].
    • (1984) Tetrahedron , vol.40 , pp. 4751-4766
    • Jung, M.E.1    Lowe J.A. III2    Lyster, M.A.3    Node, M.4    Pfluger, R.W.5    Brown, R.W.6
  • 125
    • 0038805831 scopus 로고    scopus 로고
    • G. J. Bodwell, J. Li, Angew. Chem. 2002, 114, 3395-3396; Angew. Chem. Int. Ed. 2002, 41, 3261-3262;
    • (2002) Angew. Chem. , vol.114 , pp. 3395-3396
    • Bodwell, G.J.1    Li, J.2
  • 126
    • 0037009048 scopus 로고    scopus 로고
    • G. J. Bodwell, J. Li, Angew. Chem. 2002, 114, 3395-3396; Angew. Chem. Int. Ed. 2002, 41, 3261-3262;
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 3261-3262
  • 128
    • 0036495577 scopus 로고    scopus 로고
    • b) M. Largeron, A. Neudorffer, M. Vuilhorgne, E. Blattes, M.-B. Fleury, Angew. Chem. 2002, 114, 852-855; Angew. Chem. Int. Ed. 2002, 41, 824-827;
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 824-827
  • 131
    • 0035825144 scopus 로고    scopus 로고
    • d) K. C. Nicolaou, K. Sugita, P. S. Baran, Y.-L. Zhong, Angew. Chem. 2001, 113, 213-216; Angew. Chem. Int. Ed. 2001, 40, 207-210;
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 207-210
  • 140
    • 0038467852 scopus 로고    scopus 로고
    • note
    • [12a]
  • 145
    • 4243553426 scopus 로고
    • b) A. D. Becke, Phys. Rev. 1988, A38, 3098-3100;
    • (1988) Phys. Rev. , vol.A38 , pp. 3098-3100
    • Becke, A.D.1
  • 160
    • 0037791219 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum is shown in Figure 5 in the text.


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