%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