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This paper investigates the potential for the ordered structures of LCILs to influence the stereochemical outcome of the Diels\u2013Alder reaction between cyclopentadiene and methyl acrylate. The ratio of <jats:italic>endo\u2010<\/jats:italic> to <jats:italic>exo<\/jats:italic>\u2010product from this reaction was monitored for a range of ionic liquids (ILs) and LCILs. Comparison of the <jats:italic>endo<\/jats:italic>:<jats:italic>exo<\/jats:italic> ratios in these reactions as a function of cation, anion and liquid crystallinity of the reaction media, allowed for the effects of liquid crystallinity to be distinguished from anion effects or cation alkyl chain length effects. These data strongly suggest that the proportion of <jats:italic>exo<\/jats:italic>\u2010product increases as the reaction media is changed from an isotropic IL to a LCIL. A detailed molecular dynamics (MD) study suggests that this effect is related to different hydrogen bonding interactions between the reaction media and the <jats:italic>exo<\/jats:italic>\u2010 and <jats:italic>endo<\/jats:italic>\u2010transition states in solvents with layered, smectic ordering compared to those that are isotropic.<\/jats:p>","DOI":"10.1002\/chem.201602965","type":"journal-article","created":{"date-parts":[[2016,9,23]],"date-time":"2016-09-23T07:24:40Z","timestamp":1474615480000},"page":"16113-16123","source":"Crossref","is-referenced-by-count":40,"title":["Liquid\u2010Crystalline Ionic Liquids as Ordered Reaction Media for the Diels\u2013Alder Reaction"],"prefix":"10.1002","volume":"22","author":[{"given":"Duncan W.","family":"Bruce","sequence":"first","affiliation":[{"name":"Department of Chemistry University of York  Heslington, York YO10 5DD UK"}]},{"given":"Yanan","family":"Gao","sequence":"additional","affiliation":[{"name":"Dalian Institute of Chemical Physics Chinese Academy of Sciences  457 Zhongshan Road Dalian 116023 P. 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