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Graphical Abstract: Eur. J. Org. Chem. 32/2009
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200990092
Subject(s) - chemistry , allene , cycloaddition , trifluoromethanesulfonate , nucleophile , trimethylsilyl , reagent , computational chemistry , molecule , fluoride , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , inorganic chemistry
The cover picture shows a cyclohexallene‐based starry night over the cathedral of Santiago de Compostela in northwest Spain. 1,2‐Cyclohexadiene is a highly reactive cyclic allene that is usually generated by the use of strong bases or highly nucleophilic reagents, and this limits its scope. Herein we described an improved method to generate this molecule by fluoride‐induced β‐elimination of the corresponding 6‐(trimethylsilyl)cyclohexenyl triflate. This method allows the generation of this strained cyclic allene under mild reaction conditions and with higher efficiency than classical approaches, as demonstrated by trapping experiments based on cycloaddition reactions. Details are discussed in the article by D. Peña et al. on p. 5519 ff.