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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 11, 1981 - Issue 9
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Original Articles

The 3-Methyl-1,3-butadienyl Phenyl Sulfoxide I. Preparation and Some Properties

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Pages 697-708 | Published online: 06 Dec 2006

References

  • Guittet , E. and Julia , S. 1978 . Tetrahedron Letters , : 1155 Preliminary communication
  • Evans , D. A. , Bryan , C. A. and Sims , C. L. 1972 . J. Amer. Chem. Soc. , 94 : 2891 F. A. Carey and O. Hernandez, J. C. Ey-lander, Rec. Trav. Chim., 93, 240 (1974); B. M. Trost and A. J. Bridges, J. Org. Chem., 40, 2014 (1975); Y. Gaoni, Tetrahedron Letters, 4521 (1977)
  • Jacobs , Th. L. and Mihailovski , A. 1967 . Tetrahedron Letters , : 2607 This sulfide 4 has been obtained by alternative procedures: a)
  • Huynh , C. , Ratovelomanana , V. and Julia , S. 1977 . Bull. Soc. Chim. France , : 710 );b);
  • Cohen , Th. , Gapinski , R. E. and Hutchins , R. R. 1979 . J. Org. Chem , 44 : 3599
  • Paquette , L. A. , Klobucar , W. D. and Snow , R. A. 1976 . Synth. Commun , 6 : 575 For the α-chlorination of alkyl phenyl sulfides see: P. Bakuzis, M. L. F. Bakuzis, C. C. Fortes and R. Santos, J. Org. Chem., 41, 2769 (1976); E. E. van Tamelen and E. G. Taylor, J. Amer. Chem. Soc., 102, 1202 (1980)
  • Parham , W. E. , Kajigaeshi , S. and Groen , S. H. 1972 . Bull. Chem. Soc. Japan , 45 : 509
  • Clinet , J.-C. and Julia , S. 1978 . J. Chem. Research , From 3-chloro-3-methyl-1-butyne and benzenethiol with 50% aqueous sodium hydroxide in presence of a phase transfer catalyst: (S) 125, (M) 1714
  • Chia , H.-A. , Kirk , B. E. and Taylor , D. R. 1974 . J. C. S. Perkin , Under these conditions, 2,4-dimethylpenta-2,3-diene has been isomerized into 2,4-dimethylpenta-1,3-diene: I, 1209(For other isomerizations of allenic sulfides, see H. E. Wijers, L. Brandsma and J. F. Arens, Rec. Trav. Chim., 85, 601 (1966)
  • Neef , G. , Eder , U. and Seeger , A. 1980 . Tetrahedron Letters , : 903 However, a steroidal allenic sulfoxide has been thermally isomerized into a dienylic sulfoxide
  • Okamura , H. , Mitsuhira , Y. , Miura , M. and Takei , H. 1978 . Chem. Ltters , : 517 G. H. Posner, P.-W. Tang and J. P. Mallamo, Tetrahedron Letters, 3995 (1978). For α-lithio allenyl sulfoxides, see R. C. Cookson and P. J. Parsons, J. C. S. Chem. Comm., 822 (1978)
  • Goldmann , S. , Hoffmann , R. W. , Maak , N. and Geueke , K.-J. 1980 . Chem. Ber. , 113 : 831 These compounds have probably the geometry indicated in the formulas 9 10. When treated with excess LDA then with methanol-NH4Cl-water, the (E) and (Z) 1,3-butadienyl ptolyl sulfoxides are known to give only the (E) isomer
  • Vedejs , E. and Mullins , M. 1975 . Tetrahedron Letters , : 2017
  • Sugihara , H. , Tanikaga , R. , Tanaka , K. and Kaji , A. 1978 . Bull. Chem. Soc. Japan , 51 : 655 Michael additions of some metal enolates of carbonyl compounds to simple vinyl sulfoxides are known: see the references cited in our preliminary communication1 and also: G. Tsuchihashi, S. Mita-mura and K. Ogura, ibid., 52, 2167 (1979); J. Bruhn, H. Heimgartner and H. Schmid, Helv. Chim. Acta, 62, 2630 (1979); I. Hori and T. Oishi, Tetrahedron Letters, 4087 (1979). For Michael-type additions to α-allenic sulfoxides, see R. C. Cookson and R. Gopalan, J. C. S. Chem. Comm. 608 (1978)
  • Cazes , B. , Huynh , C. , Julia , S. , Ratovelomanana , V. and Ruel , O. 1978 . J. Chem. Research , (S) 68, (M) 0957
  • Nakane , M. and Hutchinson , C. R. 1978 . J. Org. Chem. , 43 : 3922
  • Starks , Ch. M. 1971 . J. Amer. Chem. Soc. , 93 : 195 Aliquat 336 is the commercial name for tricaprylyl methyl ammonium chloride, purchased by Fluka AG. See;A. W. Herriott and D. Picker, Synthesis, 447 (1975)
  • Horner , L. and Binder , V. 1972 . Liebigs Ann. Chem. , 757 : 33
  • Birch , A. J. , Corrie , J. E. T. and Subba Rao , G. S. R. 1970 . Aust. J. Chem. , 23 : 1811
  • Blomquist , A. T. and Verdol , J. A. 1955 . J. Amer. Chem. Soc. , 77 : 78 prepared from 3-methyl-3-buten-1-ol

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