16510-81-9Relevant articles and documents
-
Oda,J. et al.
, p. 373 - 378 (1967)
-
Metalation of arylmethyl alkyl ethers
Azzena, Ugo,Pilo, Luciano,Sechi, Alessandra
, p. 12389 - 12398 (2007/10/03)
Arylmethyl alkyl ethers 1a-11 were metallated with n-BuLi or sec-BuLi in THF at different temperatures, affording α-alkoxy-substituted arylmethyllithium derivatives. At low temperature, the organometallics derived from methyl and isopropyl ethers are suff
Investigation of the stereochemistry of Fe-Cα bond cleavage when phenylcyclopropane is generated by γ-ionization of stereospecifically deuterated C5H5(CO)2 FeCHDCHDCH(OCH3)C6H5 complexes.
Brookhart, Maurice,Liu, Yumin
, p. 939 - 944 (2007/10/02)
C5H5(CO)2FeCH2CH 2CH(OCH3)C6H5, 4, and stereospecifically deuterium labeled threo-d2-C5H5-(CO) 2FeCHDCHDCH(OCH3)C6H5, 7a,b and erythro-d2-C5H5(CO) 2FeCHDCHDCH(OCH3)C6H5, 8a,b were synthesized. Treatment of compound 4 with trimethylsilyl triflate results in ionization of the γ-methoxy group and formation of phenylcyclopropane in good yields. Ionization of 7a,b gives a 1:1 mixture of cis-2,cis-3-dideuterio- and trans-2,trans-3-dideuterio-r-1-phenylcyclopropane, while ionization of 8a,b gives cis-2,trans-3-dideuterio-r-1-phenylcyclopropane. These results established that the cyclopropane ring is formed by backside attack of electrophilic Cγ on Cα with net inversion of stereochemistry at Cα. These reactions serve as models for the reactions of carbene complexes C5H5(CO)2Fe=CHR+ with alkenes to give cyclopropanes and suggest that in the transfer reactions Fe-Cα is cleaved with inversion.