By Gribble Prof , Gordon Gribble , John Joule Prof Gribble Prof
This is often the 17th annual quantity of growth in Heterocyclic Chemistry, which covers the literature released in the course of 2004 on lots of the very important heterocyclic ring structures. the quantity opens with really good experiences: Dennis Wright covers Furans as flexible Synthons for Target-Oriented and Diversity-Oriented Synthesis; and John Hepworth and Mark Heron speak about 'The Synthesis and Photochromic houses of Naphthopyrans'. the remainder chapters learn the hot literature at the universal heterocycles so as of accelerating ring measurement and the heteroatoms current. * contains new contributions from specialists within the box* Covers literature released in the course of 2004 on many of the very important heterocyclic ring structures * provides experiences on flexible Synthons for Target-Oriented and Diversity-Oriented Synthesis; and Synthesis and Photochromic homes of Naphthopyrans
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Extra resources for A Critical Review of the 2004 Literature Preceded by Two Chapters on Current Heterocyclic Topics
There appears to be a correlation between AG* and the calculated 7t-bond order for the fusion bond between the pyran and benzene rings; the more electron-rich the bond, the lower is AG* <97HCA1122>. 1 3i/-Naphtho[2,l-6]pyrans The photochromic response of the angular 3i/-naphtho[2,l-6]pyran isomer 2, is typically characterised by the production of a weak colour associated with the photochemically induced electrocyclic ring opening of the colourless pyran ring to a coloured quinoidal form on irradiation with UV light (Scheme 8).
A greater red shift but poorer colourability and increased stability of the open form are shown by the [2,3-/] 23 than by the [3,2-/] 24 isomer which were synthesised from the hydroxydibenzothiophene by the Ti-promoted and propargylation routes, respectively <02T1709>. Synthesis and photochromic properties of naphthopyrans 45 Furobenzopyrans are derived from hydroxybenzofurans using the Iwai-Ide route. However, the cyclisation is not regiospecific unless a blocking substituent is employed, and generally a mixture of angular and linear products results that is not always readily separable <95WOP05382>.
Those furans with appended diols gave bicyclic acetals 297, those with a single alcohols the hydropyrones 298 that underwent dehydration and those without a hydroxyl gave the open-chain compounds, thus generating three structural types from a common intermediate. This last diversity-oreiented example nicely illustrates the synthetic flexibility and power offered by the use of furans. It is certain that the role of furan in complex-molecule synthesis will continue to expand in many new directions.