%0 Journal Article
%A Wang, Xiao-Na
%A Krenske, Elizabeth H.
%A Johnston, Ryne C.
%A Houk, K. N.
%A Hsung, Richard P.
%D 2015
%T Torquoselective
Ring Opening of Fused Cyclobutenamides:
Evidence for a Cis,Trans-Cyclooctadienone Intermediate
%U https://acs.figshare.com/articles/journal_contribution/Torquoselective_Ring_Opening_of_Fused_Cyclobutenamides_Evidence_for_a_i_Cis_Trans_i_Cyclooctadienone_Intermediate/2039211
%R 10.1021/ja502252t.s001
%2 https://acs.figshare.com/ndownloader/files/3610527
%K ci
%K bicyclic
%K cyclobutenamides 1
%K Fused Cyclobutenamides
%K case conversion
%K Torquoselective Ring
%K ring opening
%K vinyl cyclopentenones
%X Electrocyclic
ring opening of 4,6-fused cyclobutenamides 1 under thermal
conditions leads to cis,trans-cyclooctadienones 2-E,E as transient intermediates,
en route to 5,5-bicyclic products 3. Theoretical calculations
predict that 4,5-fused cyclobutenamides
should likewise undergo thermal ring opening, giving cis,trans-cycloheptadienones, but in this case conversion to 5,4-bicyclic
products is thermodynamically disfavored, and these cyclobutenamides
instead rearrange to vinyl cyclopentenones.
%I ACS Publications