The thionophosphate-thiolophosphate photoisomerization proceeds predominantly through a non-chain radical pathway. Synthetically viable benzylation of tetrahydrofuran, propan-2-ol and olefins

Journal of the Chemical Society. Perkin Transactions 1

Volumn , Issue 3, 2001, Pages 323-332

  Yadav, Veejendra K ^a   Balamurugan, Rengarajan ^a   Parvez, Masood ^a   Yamdagni, Raghav ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; DISSOCIATION; IRRADIATION; ISOMERIZATION; MERCURY (METAL); OLEFINS; PHOSPHATES; PHOTOCHEMICAL REACTIONS; SOLVENTS;

PHOTOISOMERIZATION;

KETONES;

EID: 0035819722     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/b003501g     Document Type: Article

References (25)

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3. Heating of a toluene solution in a pressure tube at 140 °C (bath temperature) for 4-5 h gave only the starting material without any noticeable decomposition.
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8. w = 0.051. C7-C7* = 1.402(14) Å, C8-O1 = 1.190(7) Å, C8-C7-C7* = 111.0(9)°, O1-C8-C7 = 125.9(7)°, O1-C8-C7-C7* = -35.9(14)°, C6-C1-C7-C7C* = 46.7(11)°, O2-C8-C7-C7* = 149.8(10)°, O1-C8-O2-C9 = 0.8(11)°, C7-C8-O2-C9 = 175.2(6)°. For the preparation of the Z-isomer of 4 (i.e. the diphenylmaleate) and the data on it, see: H. Oda, M. Morishita, K. Fugami, H. Sano and M. Kosugi, Chem. Lett., 1996, 811.
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13. For an asymmetric C H insertion of a carbenoid into tetrahydrofuran, see: H.M.L. Davies and T. Hansen, J. Am. Chem. Soc., 1997, 119, 9075.
14. D.H.R. Barton, D. Crich and W.B. Motherwell, Tetrahedron, 1985, 41, 3901; D. Crich, Aldrichim. Acta, 1987, 20, 35; D.H.R. Barton, D. Briden, I.F. Picot and S.Z. Zard, Tetrahedron, 1987, 43, 2733. For an alternative mechanism, see: V.K. Yadav, A. Yadav, P. Pande and K.K. Kapoor, Indian J. Chem., Sect. B. 1994, 33, 1129.
15. D.H.R. Barton, D. Crich and W.B. Motherwell, Tetrahedron, 1985, 41, 3901; D. Crich, Aldrichim. Acta, 1987, 20, 35; D.H.R. Barton, D. Briden, I.F. Picot and S.Z. Zard, Tetrahedron, 1987, 43, 2733. For an alternative mechanism, see: V.K. Yadav, A. Yadav, P. Pande and K.K. Kapoor, Indian J. Chem., Sect. B. 1994, 33, 1129.
16. D.H.R. Barton, D. Crich and W.B. Motherwell, Tetrahedron, 1985, 41, 3901; D. Crich, Aldrichim. Acta, 1987, 20, 35; D.H.R. Barton, D. Briden, I.F. Picot and S.Z. Zard, Tetrahedron, 1987, 43, 2733. For an alternative mechanism, see: V.K. Yadav, A. Yadav, P. Pande and K.K. Kapoor, Indian J. Chem., Sect. B. 1994, 33, 1129.
17. D.H.R. Barton, D. Crich and W.B. Motherwell, Tetrahedron, 1985, 41, 3901; D. Crich, Aldrichim. Acta, 1987, 20, 35; D.H.R. Barton, D. Briden, I.F. Picot and S.Z. Zard, Tetrahedron, 1987, 43, 2733. For an alternative mechanism, see: V.K. Yadav, A. Yadav, P. Pande and K.K. Kapoor, Indian J. Chem., Sect. B. 1994, 33, 1129.
18. E.J. Corey and M. Chaykovsky, J. Am. Chem. Soc., 1965, 87, 1353; A. Merz and G. Mark, Angew. Chem., Int. Ed. Engl., 1973, 12, 845; L.A. Yanovskaya, V.A. Dombrovsky, O.S. Chizhov, B.M. Zolotarev, O.A. Subbotin and V.F. Kucherov, Tetrahedron, 1972, 28, 1565; D.N. Boykin, A.B. Turner and R.E. Lutz, Tetrahedron Lett., 1967, 817; Y.D. Vankar, G. Kumaravel and C.T. Rao, Synth. Commun., 1989, 19, 2181.
19. E.J. Corey and M. Chaykovsky, J. Am. Chem. Soc., 1965, 87, 1353; A. Merz and G. Mark, Angew. Chem., Int. Ed. Engl., 1973, 12, 845; L.A. Yanovskaya, V.A. Dombrovsky, O.S. Chizhov, B.M. Zolotarev, O.A. Subbotin and V.F. Kucherov, Tetrahedron, 1972, 28, 1565; D.N. Boykin, A.B. Turner and R.E. Lutz, Tetrahedron Lett., 1967, 817; Y.D. Vankar, G. Kumaravel and C.T. Rao, Synth. Commun., 1989, 19, 2181.
20. E.J. Corey and M. Chaykovsky, J. Am. Chem. Soc., 1965, 87, 1353; A. Merz and G. Mark, Angew. Chem., Int. Ed. Engl., 1973, 12, 845; L.A. Yanovskaya, V.A. Dombrovsky, O.S. Chizhov, B.M. Zolotarev, O.A. Subbotin and V.F. Kucherov, Tetrahedron, 1972, 28, 1565; D.N. Boykin, A.B. Turner and R.E. Lutz, Tetrahedron Lett., 1967, 817; Y.D. Vankar, G. Kumaravel and C.T. Rao, Synth. Commun., 1989, 19, 2181.
21. E.J. Corey and M. Chaykovsky, J. Am. Chem. Soc., 1965, 87, 1353; A. Merz and G. Mark, Angew. Chem., Int. Ed. Engl., 1973, 12, 845; L.A. Yanovskaya, V.A. Dombrovsky, O.S. Chizhov, B.M. Zolotarev, O.A. Subbotin and V.F. Kucherov, Tetrahedron, 1972, 28, 1565; D.N. Boykin, A.B. Turner and R.E. Lutz, Tetrahedron Lett., 1967, 817; Y.D. Vankar, G. Kumaravel and C.T. Rao, Synth. Commun., 1989, 19, 2181.
22. E.J. Corey and M. Chaykovsky, J. Am. Chem. Soc., 1965, 87, 1353; A. Merz and G. Mark, Angew. Chem., Int. Ed. Engl., 1973, 12, 845; L.A. Yanovskaya, V.A. Dombrovsky, O.S. Chizhov, B.M. Zolotarev, O.A. Subbotin and V.F. Kucherov, Tetrahedron, 1972, 28, 1565; D.N. Boykin, A.B. Turner and R.E. Lutz, Tetrahedron Lett., 1967, 817; Y.D. Vankar, G. Kumaravel and C.T. Rao, Synth. Commun., 1989, 19, 2181.
23. The substrate 59 was prepared from Simmons-Smith cyclopropanation of 1,3-diphenylpropene which, in turn, was made available from the Wittig reaction of benzaldehyde and the triphenylphosphorane prepared from 2-phenylethyl bromide. However, see: R. Hollis, L. Hughes, V.W. Bowry and K.U. Ingold, J. Org. Chem., 1992, 57, 4284.
24. 2O following standard reaction conditions in >90% yield.
25. 2 O following standard reaction conditions in >90% yield.