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I HO 78 Chapter 1. 41 Rearrangements Nicolaou has recently reported the use of microwave irradiation for the Claisen rearrangement of 77. 29 When repeated attempts failed to accomplish the Claisen rearrangement of 79 to allenyl ketone 80, Ley and co-workers relied on microwave irradiation to address this challenging bond construction. 31Isomers 83 and 84 were formed and the rate of the formation of 83 was examined. Reactions were completed at lower temperature and in shorter time using aqueous methanol solvent as compared to DMF.
33 73 o°CJH2C~ Et02CCHO 125 89% rt, CH2CI2 Me2N+CH21- OH 126 H I127 74% Time Ratio of 129:130 Yield o/o R i = R2 = H R1 = R2 = Me 108 R1 = H, R2 = t-BUCOp- 24 90:10 82 R i = PhC02-, R2 = H 81:19 72 24 Chapter 1. 34 At 120 "C in DMF, the cyclization of the terminal allenic double bond with simple alkenes occurred intramolecularly. While a by-product was formed, no activator was utilized. Other solvents were screened as well as ionic liquids and were found inferior to DMF in facilitating the reaction.
Intramolecular Did-Alder and Alder-Ene Reactions, SpringerVerlag, Berlin, Germany; 1984, chapter 3. [R] Trost, B. M. Ace. Chem. Res. 1 9 9 0 , 2 3 , 3 4 4 2 . Hill, R. ; Rabinovitz, M. J. Am. Chem. Soc. 1964,86, 965-966. ; Papadopoulos, M. J. Org. Chem. 1982,47,42014202. ; Koster, D. ; Arnold, R. T. J. Am. Chem. 1974, 96,42074210. Stephenson, L. ; Mattern, D. L. J. Org. Chem. 1976,41,3614-3619. Kennedy-Smith, J. ; Staben, S. ; Toste, F. D. J. Am. Chem. Soc. 2 004,126,4526-4527. [R] Vougioukalakis, G.