61415-37-0Relevant articles and documents
Efficient syntheses of four stable-isotope labeled (1R)-menthyl (1S,2S)-(+)-2-phenylcyclopropanecarboxylates
Keliher, Edmund J.,Burrell, Richard C.,Chobanian, Harry R.,Conkrite, Karina L.,Shukla, Rajesh,Baldwin, John E.
, p. 2777 - 2784 (2008/09/16)
Many carbenoid cyclopropanation reactions promoted by chiral catalysts give product mixtures reflecting impressive diastereo- and enantioselectivities. Few provide a single chiral product efficiently. This limitation has been overcome in cyclopropanations of styrene and isotopically labeled styrenes with α-diazoacetates. Convenient syntheses on a 20 g scale of each of four chiral isotopically labeled (1R)-menthyl (1S,2S)-2- phenylcyclopropanecarboxylates (the 1-d-3-13C, 1,(3S)-d2, 1,2,(3S)-d3, and 1,3,3-d3 isotopomers) of better than 99% ee have been realized. The Royal Society of Chemistry 2006.
Pd-catalyzed ring-opening copolymerization of 2-aryl-1-methylenecyclopropanes with CO to afford polyketones via alternating insertion of the two monomers and C - C bond activation of the three-membered ring
Kim, Sunwook,Takeuchi, Daisuke,Osakada, Kohtaro
, p. 762 - 763 (2007/10/03)
Pd-bpy complexes catalyze the ring-opening copolymerization of 2-aryl-1-methylenecyclopropanes with CO, affording the new polyketones composed of ring-opened structural units only. Kinetic and isotope-labeling studies revealed the mechanism of the reactio
Thermal isomerization of benzocyclobutene
Chapman, Orville L.,Tsou, Uh-Po Eric,Johnson, Jeffery W.
, p. 553 - 559 (2007/10/02)
Thermolysis of benzocyclobutene 13CH2, 99percent gives styrene labeled in the β (48percent), ortho (30percent), α (14percent), meta (4percent), and para (4percent) positions.The major labels (β and ortho) are consistent with a mechanism involving interconversions of the isomeric tolylmethylenes and the methylcycloheptatrienes.This mechanism also involves interconversion of o-tolylmethylene with o-xylylene and p-tolylmethylene with p-xylylene.A minor mechanism produces 25percent of styrene.This mechanism involves cleavage of the aryl carbon to the methylene carbon bond in benzocyclobutene followed by hydrogen transfer to produce styrene.Thermolysis of p-xylylene produced from paracyclophane gives styrene (55percent), p-xylene (31percent), benzocyclobutene (4percent), benzene (4percent), and toluene (3percent).Thermolysis of metacyclophane gives styrene (18percent), p-xylene (25percent), m-xylene (3percent), benzocyclobutene (1percent), benzene (7percent), and toluene (22percent).