Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2006, Issue 23, Pages 5207-5218Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200600406
Keywords
cyclobutene; additions; ring contractions; nucleosides; dienes
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Cyclobutene compounds are interesting intermediates that have proven to be useful in organic synthesis. This review mainly deals with preparations and reactions of some cyclobutenes disubstituted at the allylic position. Several possibilities in the area of the thermal ring opening of these compounds into dienes are explored, and some features of the selectivity of addition reactions to cyclobutenes to afford trior tetrasubstituted cyclobutanes are also examined. When suitable leaving groups are present, these cyclobutanes can yield cyclopropanes stereo specifically through ring contraction or bicyclic compounds through intramolecular cyclization. Some applications to the synthesis of nucleoside analogues and of bicyclic compounds are pointed out.
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