83577-63-3Relevant academic research and scientific papers
Preparation of a storable zinc carbenoid species and its application in cyclopropanation, chain extension, and [2,3]-sigmatropic rearrangement reactions
Voituriez, Arnaud,Zimmer, Lucie E.,Charette, Andre B.
experimental part, p. 1244 - 1250 (2010/04/26)
(Chemical Equation Presented) The formation of a new phosphate carbenoid (n-BuO)2P(O)OZnCH2I and its application in organozinc-mediated reactions is described. This carbenoid undergoes very slow degradation in solution and can be stored for several weeks at -20 °C. Its reactivity was tested with many representative alkenes and was determined to be a powerful cyclopropanating reagent, giving the corresponding cyclopropanes in 72-99% yield. The use of this carbenoid in the chain extension of 1,3-diketones and [2,3]-sigmatropic rearrangement reactions is also described. 2010 American Chemical Society.
2,3-Sigmatropic rearrangement of sulfonium ylides generated by addition of samarium carbenoids
Kunishima, Munetaka,Nakata, Daisuke,Goto, Chikako,Hioki, Kazuhito,Tani, Shohei
, p. 1366 - 1368 (2007/10/03)
Allylic sulfides are transformed into homoallylic sulfides with complete allylic inversion by treatment with SmI2 and CH2I2 in THF. The reaction will involve allylic sulfonium ylides as an intermediate, which undergoes 2,3-rearrangement.
A METHOD FOR METHYLIDENATION AND ETHYLIDENATION OF AN ALLYLIC THIOETHER LEADING TO A 2,3-SIGMATROPIC REARRANGEMENT. FAILURE OF THE SIMMONS-SMITH REACTION IN THE PRESENCE OF THIOETHERS
Kosarych, Zenyk,Cohen, Theodore
, p. 3019 - 3022 (2007/10/02)
Allylic phenylthioethers are converted in one step to homoallylic phenylthioethers by treatment with methylene iodide or ethylidene iodide in the presence of diethylzinc but not zinc-copper or zinc-silver couples; furthermore, Simmons-Smith cyclopropanati
