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Chemical Compound Review: 

Cyclobutene     cyclobutene

Synonyms: AG-H-29452, CHEBI:51206, CTK3F0910, AKOS006332479, AC1L2D2W, ...
 
 
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High impact information on cyclobutene

  • The epoxidation barriers are only slightly higher for the strained alkenes cyclopropene (DeltaE++ = 14.5 kcal/mol) and cyclobutene (DeltaE++ = 13.7 kcal/mol) than for cyclopentene (DeltaE++ = 12.1 kcal/mol), reflecting the fact there is little relief of strain in the transition state [1].
  • While the irradiation of 9 led principally via SO(2)-N bond homolysis and [1,5] sigmatropic rearrangement to generate 37, 10 proceeded via disrotatory cyclization to the exo cyclobutene 39, and 11 resisted photoisomerization [2].
  • The structure of the cyclobutene was elucidated by IR, MS, (1)H, (13)C, and (77)Se NMR, COSY, HMQC, and HMBC data and X-ray analysis [3].
 

Associations of cyclobutene with other chemical compounds

References

  1. Relative reactivity of peracids versus dioxiranes (DMDO and TFDO) in the epoxidation of alkenes. A combined experimental and theoretical analysis. Bach, R.D., Dmitrenko, O., Adam, W., Schambony, S. J. Am. Chem. Soc. (2003) [Pubmed]
  2. Direct comparison of the response of bicyclic sultam and lactam dienes to photoexcitation. Concerning the propensity of differing bond types to bridgehead nitrogen for homolytic cleavage. Paquette, L.A., Dura, R.D., Fosnaugh, N., Stepanian, M. J. Org. Chem. (2006) [Pubmed]
  3. Synthesis of 3-acyl-1-alkyl-2-alkylseleno-1-cyclobutene using alkyneselenolate. Koketsu, M., Mizutani, K., Ogawa, T., Takahashi, A., Ishihara, H. J. Org. Chem. (2004) [Pubmed]
  4. Beyond Schmittel and Myers-Saito cyclizations: rearrangements of 4-heteroatom-1,2-hexa-diene-5-ynes. Bui, B.H., Schreiner, P.R. Org. Lett. (2003) [Pubmed]
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