25152-47-0Relevant articles and documents
Effect of phenyl substitution on the lifetime and product distribution of cyclobutylidene: preference change in the rearrangements via 1,2-carbon shift and 1,2-hydrogen shift
Takahashi, Yasutake,Sakakibara, Takurou,Inaba, Makoto,Tomioka, Hideo,Koseki, Shiro,Fujimoto, Kazuyoshi,Umeda, Hiroaki
, p. 3995 - 3999 (2006)
Steady state and laser flash photolytic experiments with precursors 6 and 11 revealed that diphenyl substitution affects the lifetime and reaction mode of cyclobutylidene. 2,2-Diphenylcyclobutylidene 3 (τ 0.1 ns) produces methylenecyclopropane 1 via 1,2-carbon in significant preference to the positional isomer 2 or cyclobutene 4. On the other hand, 3,3-diphenylcyclobutylidene 5 (τ = ca. 4 ns) gives 1,2-hydrogen shift product 4 more favorably than 1,2-carbon shift product 2 together with formal carbene dimer 14. MRMP2//MP2 calculations afford useful results to understand the interrelationship among substitution, structure, and reactivity.
Intermediacy of cyclobutylidene in photochemical methylenecyclopropane rearrangement
Takahashi, Yasutake,Mori, Yoko,Nakamura, Akiko,Tomioka, Hideo
, p. 8415 - 8418 (2007/10/03)
Methylenecyclopropane 1 undergoes photochemical rearrangement to 2. Intervention of cyclobutylidene 3 explains not only the rearrangement but also newly obtained products such as cyclobutene 4 and cyclobutylidenecyclobutane 6. Experiments designed to generate cyclobutylidene 3 independently have provided some support for the intermediacy of 3.
Chloropalladation of Phenyl-Substituted Methylenecyclopropanes
Dallas, Bruce K.,Hughes, Russell P.,Schumann, Karen
, p. 5380 - 5383 (2007/10/02)
The chloropalladation reactions of methylenecyclopropanes bearing phenyl substituents on the cyclopropane ring are shown to involve 1,3 addition of the elements of Pd-Cl to the organic molecule, with cleavage of the 2,3 ? bond of the ring.Chloropalladatio
