By Michael Harmata
This quantity provides paintings from six various teams engaged on numerous facets of cycloaddition chemistry. Jos? Mascare?as offers us a really fascinating account of the chemistry of &Bgr;-alkoxy-&ggr;-pyrones and similar species. Al Padwa and Chris Staub speak about extra advances in rhodium carbenoid chemistry and the bizarre cycloaddition strategies attainable with those intermediates. greater order cycloadditions mediated through transition metals spotlight Jim Rigby's replace on his group's efforts during this region. Lily Lee and John Snyder current us with a close account of the indole ring as a dienophile, demanding us to think about the untapped power during this zone. Brian Keay and Ian Hunt talk about the intramolecular Diels-Alder reactions of furan; a file that's either top-notch technological know-how, and what can be a nice studying instrument for college kids who have to see how basic chemical rules can and will be utilized to artificial difficulties. ultimately, Kay Brummond introduces us to a brand new model of the Pauson-Khand reactions, person who will without doubt be additional exploited in effective methods through her workforce good into the longer term.
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Extra info for Advances in Cycloaddition, Volume 6 (Advances in Cycloaddition) (Advances in Cycloaddition)
64. -L. Tandem Organic Reactions; Wiley: New York, 1992. (b) Tietze, L. E; Beifuss, U. Angew. , Int. Ed. Engl. 1993, 32, 131. (c) Tietze, L. E Chem. Rev. 1996, 96, 115. (d) Grigg, R. Tetrahedron Symposia-In-Print Number 62, 1996, 52, 11385. (e) Bunce, R. A. Tetrahedron 1995, 51, 13103. (f) Parsons, P. ; Penkett, C. ; Shell, A. J. Chem. Rev. 1996, 96, 195. ; Neier, R. Synthesis 1998, 227. 65. Roddguez, J. ; Mascarefias, J. L. J. Org. Chem. 1999, 64, 966. 66. Several asymmetric [4+3] annulation methods to oxabicyclic compounds have been developed, see: (a) Davies, H.
The formation of this compound was explained according to the mechanistic pathway indicated in Scheme 29. HO 0==~~/0 + I 0 \ 45 Me O. DME o~~)r'~~} reflux = Ph 6~, \ 33% 73 Me I i ! 0 0 I 0, I 0 ....... "~ Me Me Scheme 29. 25 The Chemistry of fl-Alkoxy-y- Pyrones O DME reflux o _,o § IO 69 ~' Me 0 \----/ 36% I O Me 74 ss '" OJ Scheme 30. Curiously, the use of maltol (69) as pyrone partner led to the major isolated product being the polycycle 74. The formation of this compound was explained assuming a carbon rather than an oxygen trapping by benzyne of the initial [5+2] adduct, followed by intramolecular cyclization to give a cyclobutane (Scheme 30).
67. (a) Pham, V. ; Charlton, J. L. J. Org. Chem. 1995, 60, 8051. (b) Araldi, G. ; Prakash, K. R. ; Kozikowski, A. P. J. Chem. , Chem. Commun. 1997, 1875. 68. L6pez, E M. S. Thesis, Santiago de Compostela, 1998. 69. ; Ohkata, K. Heterocycles 1997, 45, 2097.