03735nam a22005655i 4500 978-981-97-0787-4 DE-He213 20251030111807.0 cr nn 008mamaa 240405s2024 si | s |||| 0|eng d 9789819707874 978-981-97-0787-4 10.1007/978-981-97-0787-4 doi QD241-441 PNN bicssc SCI013040 bisacsh PNN thema Ito, Tomohiro. author. aut http://id.loc.gov/vocabulary/relators/aut 74798 Synthesis of Medium-Sized Cycloalkenes via Fused-Cyclobutenes [electronic resource] / by Tomohiro Ito. 1st ed. 2024. Singapore : Springer Nature Singapore : Imprint: Springer, 2024. XII, 129 p. 162 illus., 25 illus. in color. online resource. text txt rdacontent computer c rdamedia online resource cr rdacarrier text file PDF rda Springer Theses, Recognizing Outstanding Ph.D. Research, 2190-5061 Introduction -- Synthesis of Functionalized Medium-Sized trans-Cycloalkenes by 4π Electrocyclic Ring Opening Alkylation Cascade -- Synthesis of γ-Aryl Medium Sized Cyclic Enones by 4π Electrocyclic Ring Opening Heck Matsuda Arylation Sequence -- Asymmetric Organocatalytic [2+2] Cycloaddition Affording Bicyclo[n.2.0]alkenes -- Conclusion -- Experiments. This book explains the existence of the intermediate using two approaches: computational chemistry and coordination chemistry. In this book, the author has developed new methods for synthesizing medium-sized cycloalkenes by utilizing the 4π-electrocyclic reaction of fused-cyclobutenes. The fundamental and most important strategy and feature of the work are as follows: first, cyclobutene is used as a readily available raw material with high-strain energy to generate more strained medium-sized cis,trans-cycloalkadiene molecules. Second, by judiciously selecting the reaction conditions, the short-lived intermediate (medium-sized cis,trans-cycloalkadiene) can be converted to medium-sized cis- or trans-cycloalkenes. For the former, the generation of the medium-sized cis,trans-cycloalkadiene intermediate is greatly affected by the substituent on the cyclobutene, and there are few examples of its generation confirmed at room temperature. Regarding the latter, the synthesis of trans-cycloalkenes is noteworthy in terms of establishing a new synthetic methodology and providing one of the few asymmetric synthesis methods, which has not been achieved before. Readers of this book can gain novel insights into strained molecules involved not only in small-sized cycloalkenes but also in medium-sized ones. Chemistry, Organic. 65325 Chemistry. Medicinal chemistry. Pharmacology. 67844 Organic Chemistry. 65327 Chemical Synthesis. 68822 Medicinal Chemistry. Pharmacology. 67844 SpringerLink (Online service) Springer Nature eBook Printed edition: 9789819707867 Printed edition: 9789819707881 Printed edition: 9789819707898 Springer Theses, Recognizing Outstanding Ph.D. Research, 2190-5061 66370 https://doi.org/10.1007/978-981-97-0787-4 ZDB-2-CMS ZDB-2-SXC 58977 58977