Literature DB >> 26611657

High Reactivity of Strained Seven-Membered-Ring trans-Alkenes.

Jillian R Sanzone1, K A Woerpel2.   

Abstract

trans-Oxasilacycloheptenes are highly reactive strained alkenes. Competition reactions showed that these seven-membered ring trans-alkenes underwent [4+2] cycloaddition reactions faster than a trans-cyclooctene. They also reacted with quinones and dimethyl acetylenedicarboxylate to form adducts with high diastereoselectivity. Kinetic studies showed that ring strain increases nucleophilicity by approximately 10(9).
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkenes; cycloaddition; cycloheptenes; silicon; strained molecules

Year:  2015        PMID: 26611657     DOI: 10.1002/anie.201510056

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  3 in total

1.  Studies on the Stability and Stabilization of trans-Cyclooctenes through Radical Inhibition and Silver (I) Metal Complexation.

Authors:  Yinzhi Fang; Joshua C Judkins; Samantha J Boyd; Christopher W Am Ende; Katarina Rohlfing; Zhen Huang; Yixin Xie; Douglas S Johnson; Joseph M Fox
Journal:  Tetrahedron       Date:  2019-05-26       Impact factor: 2.457

2.  Flow Photochemical Syntheses of trans-Cyclooctenes and trans-Cycloheptenes Driven by Metal Complexation.

Authors:  Jessica E Pigga; Joseph M Fox
Journal:  Isr J Chem       Date:  2019-10-10       Impact factor: 3.333

3.  Large-Scale Flow Photochemical Synthesis of Functionalized trans-Cyclooctenes Using Sulfonated Silica Gel.

Authors:  Ampofo Darko; Samantha J Boyd; Joseph M Fox
Journal:  Synthesis (Stuttg)       Date:  2018-12       Impact factor: 3.157

  3 in total

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