138089-67-5Relevant academic research and scientific papers
Enantioselective Cyclobutenylation of Olefins Using N-Sulfonyl-1,2,3-Triazoles as Vicinal Dicarbene Equivalents
Burns, Noah Z.,Mercer, Jaron A. M.,Patel, Sajan C.,Smith, Myles W.,Suzuki, Kensuke
supporting information, p. 6530 - 6535 (2021/09/02)
Cyclobutenes are highly useful synthetic intermediates as well as important motifs in bioactive small molecules. Herein, we report a regio-, chemo-, and enantioselective synthesis of cyclobutenes from olefins using N-sulfonyl-1,2,3-triazoles as vicinal dicarbene equivalents or alkyne [2 + 2] cycloaddition surrogates. Terminal and cis-olefins can be transformed into enantioenriched cyclopropanes via rhodium catalysis. Then, in one pot, treatment of these intermediates with tosyl hydrazide and base effects diazo formation followed by rhodium-catalyzed ring expansion to yield enantioenriched cyclobutenes. These cyclobutenes can be transformed into highly substituted, enantioenriched cyclobutanes, including structures relevant to natural product scaffolds.
On the Thermal Rearrangement of the Bicyclobutane System. A Kinetic Investigation of the Conversion of Tricyclo2,7>heptanes into Bicyclohept-6-enes
Christl, Manfred,Stangl, Roland,Jelinek-Fink, Hans
, p. 485 - 498 (2007/10/02)
Tricyclo2,7>heptane (7), its 1- (20) and 2-phenyl derivatives (22), tetracyclo2,4.03,5>octane (17), 1,2,3,4-tetrahydro-1,2,3-methenonaphthalene (25) as well as its 1- (35), 2- (32), and 3-phenyl derivatives
Redox-Photosensitized Reactions. 5. Redox-Photosensitized Ring Cleavage of 1,1a,2,2a-Tetrahydro-7H-cyclobutindene Derivatives: Mechanism and Structure-Reactivity Relationship
Majima, Tetsuro,Pac, Chyongjin,Sakurai, Hiroshi
, p. 5265 - 5273 (2007/10/02)
The mechanistic aspects of the redox-photosensitized chain cycloreversion of trans,syn-indene dimer 1 have been investigated in detail.The ? complex of 1 with the cation radical of phenanthrene (and selected other aromatic hydrocarbons) that is generated by photochemical electron transfer with p-dicyanobenzene has been shown to be a key intermediate by way of which the cycloreversion of 1 rapidly occurs without the formation of its cation radical; the rate constant for the cycloreversion has been determined to be 1*109 s-1.Redox photosensitization has been applied to the other related compounds and it has been found that the cyclobutanes which can undergo redox-photosensitized ring cleavage possess the phenyl group at C2.The importance of through-bond interactions between the two ?-electron system is discussed.
