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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 5, 1975 - Issue 4
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Original Articles

Regioselective Intramolecular Carbon-Hydrogen Insertion in Copper-Catalyzed Carbenoid Decompositions of cis-1-Methyl-3-Arylcyclohexane-1-Diazomethyl Ketones : Some Synthetic Applications

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Pages 275-281 | Received 18 Feb 1975, Published online: 05 Dec 2006

References

  • Ghatak , U. R. and Chakrabarty , S. 1972 . J. Amer. Chem. Soc. , 94 : 4756
  • Dauben , W. G. and Dietsche , T. J. 1972 . J. Org. Chem. , 37 : 1212 See for examples and References therein
  • Kitadani , M. , Ito , K. and Yoshikoshi , A. 1971 . Bull. Chem. Soc., Japan , 44 : 3431 cf. U. R. Ghatak, P. C. Chakraborti, B. C. Ranu and B. Sanyal, J. C. S. Chem. Comm., 548 (1973)
  • Wenkert , E. , Mylari , B. L. and Davis , L. L. 1968 . J. Amer. Chem. Soc. , 90 : 3870
  • Wolff , S. and Agosta , W. C. 1973 . J. Org. Chem. , 38 : 1694
  • Chakrabarti , J. K. , Szinai , S. S. and Todd , A. 1970 . J. Chem. Soc., C , : 1303
  • Ledon , H. , Linstrumelle , G. and Julia , S. 1973 . Bull. Soc. Chim., Fr. , : 2071 Inter al
  • von Doering , W. E. and Knox , L. H. 1961 . J. Amer. Chem. Soc. , 83 : 1989 D. S. Wulfman, B. W. Peace and E. K. Steffen, Chem. Comm., 1360 (1971)
  • Ghatak , U. R. , Dasgupta , R. and Chakravarty , J. 1974 . Tetrahedron , 30 : 187
  • Chakravarty , N. K. and Banerjee , D. K. 1946 . J. Indian Chem. Soc. , 23 : 377
  • Whitmore , W. F. and Roberts , C. W. 1948 . J. Org. Chem. , 13 : 31
  • This compound was prepared in an overall yield of 46–50% from 3-methylcyclohex-2-enone by a modified sequence of conjugate HCN addition (aq-KCN-EtOH, reflux), alkaline hydrolysis in situ (aq KOH, reflux) and esterification (MeOH-H2SO4-cat.H3BO3, reflux) of the crude acid
  • Chakrabortty , P. N. , Dasgupta , R. , Dasgupta , S. K. , Ghosh , S. R. and Ghatak , U. R. 1972 . Tetrahedron , 28 : 4653
  • The ketone 10a has been synthesized in an unambiguous route from 3 in an overall yield of ca. 10% through the following sequence. Conversion4b of 3 to 12 (bp 135–137°/0.6 mm) followed by conjugate addition of C6H5MgBr in presence of CuI, saponification (aq-ethylene glycol-KOH, reflux), decarboxylation (180–200°), esterification with ethereal soln. of CH2N2, Dieckmann cyclisation of the resulting diester (t-BuOK-C6H6, reflux), and finally decarboxylation (5% aq. EtOH-KOH, reflux) of the crude β-ketoester to 10a

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