Possibility of [1,5] Sigmatropic Shifts in Bicyclo[4.2.0]octa-2,4-dienes

• Published in: Journal of organic chemistry Vol. 80; no. 5; pp. 2609 - 2620
• Main Authors: Goossens, Hannelore, Winne, Johan M, Wouters, Sebastian, Hermosilla, Laura, De Clercq, Pierre J, Waroquier, Michel, Van Speybroeck, Veronique, Catak, Saron
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 06.03.2015; Amer Chemical Soc
• Subjects: Alkenes - chemistry; Bridged Bicyclo Compounds - chemistry; Chemistry; Chemistry, Organic; esters; Molecular Structure; organic chemistry; Physical Sciences; Science & Technology; temperature; Thermodynamics; DENSITY FUNCTIONALS; ORGANIC-SYNTHESIS; MOLECULAR-ORBITAL METHODS; STEREOCONTROLLED TOTAL-SYNTHESIS; DIELS-ALDER REACTION; AB-INITIO; PERICYCLIC-REACTIONS; ENDIANDRIC ACID CASCADE; WALK REARRANGEMENT; 2ND-ORDER PERTURBATION-THEORY

The thermal equilibration of the methyl esters of endiandric acids D and E was subject to a computational study. An electrocyclic pathway via an electrocyclic ring opening followed by a ring flip and a subsequent electrocyclization proposed by Nicolaou [ Nicolaou K. C. ; Chen J. S. Chem. Soc. Rev. 2...