Torquoselective Ring Opening of Fused Cyclobutenamides: Evidence for a Cis,Trans-Cyclooctadienone Intermediate

[Image: see text] 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 t...

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Autores principales: Wang, Xiao-Na, Krenske, Elizabeth H., Johnston, Ryne C., Houk, K. N., Hsung, Richard P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4353010/
https://www.ncbi.nlm.nih.gov/pubmed/24992255
http://dx.doi.org/10.1021/ja502252t
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author Wang, Xiao-Na
Krenske, Elizabeth H.
Johnston, Ryne C.
Houk, K. N.
Hsung, Richard P.
author_facet Wang, Xiao-Na
Krenske, Elizabeth H.
Johnston, Ryne C.
Houk, K. N.
Hsung, Richard P.
author_sort Wang, Xiao-Na
collection PubMed
description [Image: see text] 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.
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spelling pubmed-43530102015-07-03 Torquoselective Ring Opening of Fused Cyclobutenamides: Evidence for a Cis,Trans-Cyclooctadienone Intermediate Wang, Xiao-Na Krenske, Elizabeth H. Johnston, Ryne C. Houk, K. N. Hsung, Richard P. J Am Chem Soc [Image: see text] 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. American Chemical Society 2014-07-03 2014-07-16 /pmc/articles/PMC4353010/ /pubmed/24992255 http://dx.doi.org/10.1021/ja502252t Text en Copyright © 2014 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Wang, Xiao-Na
Krenske, Elizabeth H.
Johnston, Ryne C.
Houk, K. N.
Hsung, Richard P.
Torquoselective Ring Opening of Fused Cyclobutenamides: Evidence for a Cis,Trans-Cyclooctadienone Intermediate
title Torquoselective Ring Opening of Fused Cyclobutenamides: Evidence for a Cis,Trans-Cyclooctadienone Intermediate
title_full Torquoselective Ring Opening of Fused Cyclobutenamides: Evidence for a Cis,Trans-Cyclooctadienone Intermediate
title_fullStr Torquoselective Ring Opening of Fused Cyclobutenamides: Evidence for a Cis,Trans-Cyclooctadienone Intermediate
title_full_unstemmed Torquoselective Ring Opening of Fused Cyclobutenamides: Evidence for a Cis,Trans-Cyclooctadienone Intermediate
title_short Torquoselective Ring Opening of Fused Cyclobutenamides: Evidence for a Cis,Trans-Cyclooctadienone Intermediate
title_sort torquoselective ring opening of fused cyclobutenamides: evidence for a cis,trans-cyclooctadienone intermediate
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4353010/
https://www.ncbi.nlm.nih.gov/pubmed/24992255
http://dx.doi.org/10.1021/ja502252t
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