Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 22, 1992 - Issue 11
51
Views
18
CrossRef citations to date
0
Altmetric
Original Articles

2-Trialkylstannyl-5-tert-butoxyfurans: Convenient 5-Substituted-2(3H)-Furanone Synthons

Pages 1627-1643 | Received 07 Feb 1992, Published online: 23 Sep 2006

References

  • Meanwell , N. A. and Seiler , S. M. 1990 . Drugs of the Future , 15 : 369
  • Barton , D. and Ollis , W. D. 1979 . Comprehensive Organic Chemistry , Vol. 4 , 87 – 88 . Oxford : Pergamon Press . (b) Vol. 2, pp. 790–793
  • Berliner , E. 1949 . Organic Reactions , Vol. 5 , 229 – 289 . London : John Wiley & Sons, Inc. .
  • Rao , Y. S. 1964 . Chem. Rev. , 64 : 353 (a), (b) Lipshutz, B.H., Chem. Rev., 1986, 86, 795
  • Pelter , A. and Rowlands , M. 1987 . Tetrahedron Letters , 28 : 1203 (a), (b) Kuwajima, I. and Urabe, H., Tetrahedron Letters, 1981, 22, 5191
  • Kraus , G. A. , Cho , H. , Crowley , S. , Roth , B. , Sugimoto , H. and Prugh , S. 1983 . J. Org. Chem. , 48 : 3439 (b) Kraus, G.A. and Roth, B., J. Org. Chem., 1978, 43, 4923
  • Manuscript in preparation
  • Milstein , D. and Stille , J. K. 1979 . J. Am. Chem. Soc. , 101 : 4992 (a), (b) Stille, J.K., Angew. Chem. Int. Ed. Engl., 1986, 25, 508. (c) Bailey, T.R., Tetrahedron Letters 1986, 27, 4407
  • Kraus , G. A. and Sugimoto , H. 1978 . J. C. S. Chem. Comm. , : 30
  • Still , W. C. , Kahn , M. and Mitra , A. J. 1978 . J. Org. Chem. , 43 : 2923
  • Farina , V. 1991 . J. Org. Chem. , 56 : 4985 For a new chromatographic procedure see -
  • Kosugi , M. , Koshiba , M. , Atoh , A. , Sano , H. and Migita , T. 1986 . Bull. Chem. Soc. Jpn. , 59 : 677
  • 2-Bromoanisole underwent coupling with la to give the t-butoxyfuran as an inseparable mixture with unreacted 2-bromoanisole (65% crude yield). Colorless oil (bath 105–115°/0.1 mm): IR (film) 2975, 1594, 1494, 1250, 1163, 750 cm-1, 1H NMR (CDCl3) δ 1.42 (s, 9H), 3.91 (s, 3H), 5.50 (d, J=3.6 Hz, 1H), 6.81 (d, J=3.6 Hz, 1H), 6.90–7.00 (m, 2H), 7.15 (m, 1H), 7.73 (d, J=7.7 Hz, 1H), MS m/e 247 (MH+)
  • Green , T. W. and Wuts , P. G.M. 1991 . Protective Groups in Organic Synthesis , 385 – 397 . New York : Wiley Interscience .
  • Child , R. G. , Osterberg , A. C. , Arnold , C. , Sloboda , A. E. and Tomcufcik , A. S. 1977 . J. Pharm. Sci. , 66 : 466
  • Jakobiec , T. , Milian , A. and Zawisza , T. 1976 . J. Pharmacol. Pharm. , 28 : 537

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.