Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 9, 1979 - Issue 1
88
Views
10
CrossRef citations to date
0
Altmetric
Original Articles

Phosphoric Acid Systems, Part 8. An Improved Procedure for the Phenol-Dienone Rearrangement of Sterically Hindered Phenols

, &
Pages 5-10 | Received 09 May 1978, Published online: 05 Dec 2006

References

  • Pearson , D. E. , Frazer , M. G. , Frazer , V. S. and Washburn , L. C. Synthesis , 621 Part 7
  • Ershov , V. V. , Volod'kin , A. A. , Prohof'ev , A. I. and Solodovnikov , S. P. 1973 . Russ. Chem. Revs. , 42 : 740
  • Ershov , V. V. , Volod'kin , A. A. and Bogdanov , G. N. 1963 . Russ. Chem. Revs. , 32 : 75
  • Waring , A. J. 1966 . Advances in Alicyclic Chemistry , Vol 1 , 129 New York, N. Y. : Academic Press .
  • Nilsson , A. , Ronlán , A. and Parker , V. D. 1975 . Tetrahedron Letters , : 1107
  • McKillop , A. , Perry , D. H. , Edwards , M. , Antus , S. , Farkas , L. , Nógrádi , M. and Taylor , E. C. 1976 . J. Org. Chem. , 41 : 282
  • Müller , E. , Ley , K. and Kiedaisch , W. 1954 . Chem. Ber. , 87 : 1605
  • Ershov , V. V. and Volod'kin , A. A. 1962 . Izv. Akad. Nauk. SSSR, Otd. Khim. Nauk. , : 1925
  • Forman , L. and Sears , W. C. 1954 . J. Am. Chem. Soc. , 76 : 4977 These workers observed de-t-butylation in the reaction of 3-methyl-4,6-di-t-butylphenol with excess bromine or chlorine
  • Kalibabchuk , N. N. and Pokhodenko , V. D. 1968 . J. Org. Chem. USSR , 4 : 320
  • Volod'kin , A. A. and Ershov , V. V. 1962 . Izv. Akad. Nauk. SSSR, Otd. Khim. Nauk. , : 1931
  • Ley , K. , Müller , E. , Mayer , R. and Scheffler , K. 1958 . Chem. Ber. , 91 : 2670
  • Mills , L. E. U. S. Patent, 2,221,807 .
  • Romadane , I. and Chizhikova , V. P. 1971 . Latv. PSR Zinat. Akad. Vestis. Kim. Ser. , : 563 C. A., 76, 13996y
  • Cyclic phosphate esters such as ethylene phosphate may react faster than TMP with HX.13
  • Westheimer , F. H. 1968 . Acc. Chem. Res. , 1 : 70
  • Caló and Lopez , L. 1975 . J. C. S. Chem. Commum. , : 212
  • Caló , V. , Lopez , L. and Valentino , D. S. 1978 . Synthesis. , : 139 These authors employed cyclohexene epoxide as a scavenger for HBr in the free - radical bromination of ketones
  • Preliminary experiments have indicated that TMP may not be as useful in the halogenation of amines. For instance, aniline was brominated to a mixture of p-bromoaniline (5%), 2,4,6-tribromoaniline (1%), and an unidentified water soluble compound. However, dimethylaniline gave p-bromodimethylaniline in 71% yield

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.