10.1021/ja502252t.s004
Xiao-Na Wang
Xiao-Na
Wang
Elizabeth H. Krenske
Elizabeth H.
Krenske
Ryne C. Johnston
Ryne C.
Johnston
K. N. Houk
K. N.
Houk
Richard P. Hsung
Richard P.
Hsung
Torquoselective
Ring Opening of Fused Cyclobutenamides:
Evidence for a <i>Cis,Trans</i>-Cyclooctadienone Intermediate
American Chemical Society
2015
ci
bicyclic
cyclobutenamides 1
Fused Cyclobutenamides
case conversion
Torquoselective Ring
ring opening
vinyl cyclopentenones
2015-12-17 04:12:30
Dataset
https://acs.figshare.com/articles/dataset/Torquoselective_Ring_Opening_of_Fused_Cyclobutenamides_Evidence_for_a_i_Cis_Trans_i_Cyclooctadienone_Intermediate/2039205
Electrocyclic
ring opening of 4,6-fused cyclobutenamides <b>1</b> under thermal
conditions leads to <i>cis,trans</i>-cyclooctadienones <b>2</b>-<i>E</i>,<i>E</i> as transient intermediates,
en route to 5,5-bicyclic products <b>3</b>. Theoretical calculations
predict that 4,5-fused cyclobutenamides
should likewise undergo thermal ring opening, giving <i>cis,trans</i>-cycloheptadienones, but in this case conversion to 5,4-bicyclic
products is thermodynamically disfavored, and these cyclobutenamides
instead rearrange to vinyl cyclopentenones.