53966-52-2Relevant academic research and scientific papers
Hindered organoboron groups in organic chemistry. 25. The condensation of aliphatic aldehydes with dimesitylboryl stabilised carbanions to give alkenes
Pelter,Smith,Elgendy
, p. 7119 - 7132 (2007/10/02)
In the presence of protic acids the condensation of aliphatic aldehydes with dimesitylboryl stabilised carbanions results in alkenes. In the presence of strong acids such as HCl or CF3SO3H, the products contain > 90% of E-alkenes in all cases tried. When acetic acid is used, the Z-alkenes may result predominantly, particularly in the cases of R(S)CHO and R(t)CHO.
HINDERED ORGANOBORON GROUPS IN ORGANIC SYNTHESIS. 14. STEREOSELECTIVE SYNTHESIS OF ALKENES BY THE BORON-WITTIG REACTION USING ALIPHATIC ALDEHYDES
Pelter, Andrew,Smith, Keith,Elgendy, Said,Rowlands, Martin
, p. 5647 - 5650 (2007/10/02)
In the presence of HX, carbanions Mes2BCHLiR1 react with aliphatic aldehydes to give alkenes.The stereochemistry of product alkene depends upon the nature of HX.
HINDERED ORGANOBORON GROUPS IN ORGANIC SYNTHESIS. 13. THE DIRECT PRODUCTION OF KETONES FROM ALIPHATIC ALDEHYDES BY A UNIQUE VARIANT OF THE BORON-WITTIG REACTION
Pelter, Andrew,Smith, Keith,Elgendy, Said,Rowlands, Martin
, p. 5643 - 5646 (2007/10/02)
In the presence of trifluoroacetic anhydride or N-chlorosuccinimide, aliphatic aldehydes react with dimesitylboron stabilised carbanions to give after work up, the corresponding ketones, a process wich is unique among Wittig type reactions.Yields of ketones are satisfactory in all cases except those involving the anion derived from the parent compound dimesitylmethylborane, wich give the corresponding alkenes.
