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

Xiaona Wang | Zendy; Elizabeth H. Krenske | Zendy; Ryne C. Johnston | Zendy; K. N. Houk | Zendy; Richard P. Hsung | Zendy

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

Author(s) -

Xiaona Wang,

Elizabeth H. Krenske,

Ryne C. Johnston,

K. N. Houk,

Richard P. Hsung

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja502252t

Subject(s) - chemistry , bicyclic molecule , ring (chemistry) , electrocyclic reaction , stereochemistry , transient (computer programming) , computational chemistry , organic chemistry , computer science , operating system

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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