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Stereoelectronic Effects on Dienophile Separation Influence the Diels–Alder Synthesis of Molecular Clefts
Author(s) -
Stoermer Martin J.,
Wickramasinghe Wasantha A.,
Byriel Karl A.,
Hockless David C. R.,
Skelton Brian W.,
Sobolev Alexandre N.,
White Allan H.,
Mak Jeffrey Y. W.,
Fairlie David P.
Publication year - 2017
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.201701319
Subject(s) - cyclopentadiene , chemistry , cycloaddition , diene , adduct , reactivity (psychology) , diels–alder reaction , conjugated system , pericyclic reaction , stereoselectivity , stereochemistry , organic chemistry , computational chemistry , catalysis , polymer , medicine , natural rubber , alternative medicine , pathology
The formal cycloaddition adduct of 1,4‐benzoquinone with two equivalents of cyclopentadiene is a scaffold with two non‐conjugated alkenes. Both alkenes undergo endo [4+2] cycloaddition with a diene to form a rigid U‐shaped molecular cleft. Here we show experimental, computational and structural evidence that π interactions between the alkenes affect structural rigidity, Diels–Alder reactivity, cleft formation and host–guest capture.