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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 3, 1973 - Issue 4
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Original Articles

Reduction and Reductive Alkylation of α-tert-Butylthio Carbonyl Compounds. An Efficient Method for Stepwise α-Alkylation of Esters, Nitriles and Ketones Via the α-Tert-Butylthio Derivatives

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Pages 265-272 | Received 06 Jun 1973, Published online: 05 Dec 2006

References

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  • Smith , H. A. , Huff , B. J. L. , Powers , W. J. III and Caine , D. 1967 . J. Org. Chem. , 32 : 2851
  • Weiss , M. J. , Schaub , R. E. , Allen , G. R. Jr. , Poletto , J. F. , Pidacks , C. , Conrow , R. B. and Coscia , C. J. 1964 . Tetrahedron , 20 : 357
  • McChesney , J. D. and Wycpalek , A. F. 1971 . Chem. Commun. , : 542
  • Coates , R. M. and Sowerby , R. L. 1971 . J. Amer. Chem. Soc. , 93 : 1027
  • Corey , E. J. and Seebach , D. 1966 . J. Org. Chem. , 31 : 4097
  • Peterson , D. J. 1967 . ibid. , 32 : 1717
  • Gassman , P. G. and Richmond , G. D. 1966 . J. Org. Chem. , 31 : 2355 The reactivity of which are expected, however, to be still retained and probably be higher than those of the related α-sulfinyl and α-sufonyl carbonyl compounds
  • Carroll , N. M. and O'Sullivan , W. I. 1965 . ibid. , 30 : 2830
  • House , H. O. and Larson , J. K. 1968 . ibid. , 33 : 61
  • Blandsma , L. 1970 . Rec. Trav. Chim. Pays-Bas , 89 : 593 and references cited therein
  • House , H. O. , Gall , M. and Olmstead , H. D. 1971 . J. Org. Chem. , 36 : 2361
  • Conia , J.-M. 1963 . Rec. Chem. Progr. , 24 : 43 For general discussion and examples, see
  • House , H. O. 1967 . ibid. , 28 : 99
  • House , H. O. 1972 . Modern Synthetic Reactions, Second edition 492 Menlo Park, California : W. A. Benjamin, Inc. .
  • Mundy , B. P. 1972 . J. Chem. Education , 49 : 91
  • Arapakos , P. G. 1967 . J. Amer. Chem. Soc. , 89 : 6794
  • Nagata , W. 1969 . Nippon Kagaku Zasshi , 90 : 837
  • Darling , S. D. , Devgan , O. N. and Cosgrove , R. E. 1970 . J. Amer. Chem. Soc. , 92 : 696
  • “ n ” . In t Use of lithium-naphthalene/THF was also commonly applicable to the substituted ketones 3d and the esters 3b. However, an intramolecular migration of t-butyl-thio group to the ester function was observed in the latter case. Thus, on alkylation with methyl iodide, 3a (R1 = R2 = n-Am) gave-butyl l-methyl, l-amyl thioheptanoate

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