3635-94-7Relevant articles and documents
Volger et al.
, p. 218 (1969)
Cyclopropene: A new simple synthesis and Diels-Alder reactions with cyclopentadiene and 1,3-diphenylisobenzofuran
Binger, Paul,Wedemann, Petra,Goddard, Richard,Blinker, Udo H.
, p. 6462 - 6464 (2007/10/03)
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ORBITAL CONTROL OF STEREOCHEMISTRY IN ACID-CATALYSED ADDITION REACTIONS OF ENDO-TRICYCLO2.4>OCT-6-ENE
Battiste, Merle A.,Coxon, James M.,Simpson, Gregory W.,Steel, Peter J.
, p. 3137 - 3144 (2007/10/02)
The reaction of endo-tricyclo2.4>oct-6-ene 1 with methanol in the presence of catalytic amounts of toluene-p-sulphonic acid has been shown to give 2-exo- and endo-methoxybicyclooct-3-ene (2c) and (2d) and 2-endo-methoxybicyclooct-6-ene (13).The formation of 2-exo-methoxybicyclooct-3-ene (2c), the major product of reaction, has been probed by deuterium labelling experiments and a series of 6-exo-7-exo-dideuterobicyclooct-3-enes synthesised for (2)H, (1)H and (13)C NMR spectral analysis in order unambiguously to determine the stereochemistry of proton attack on endo-tricyclo2.4>oct-6-ene ( 1).The formation of 2-exo-methoxybicyclooct-3-ene (2c) has been determined to involve corner protonation of the cyclopropyl moiety and skeletal rearrangement to an allylic cation with a small but measurable memory effect.