3533-63-9Relevant articles and documents
Silylamination of electrophilic alkynes
Baines, Kim M.,McOnie, Sarah L.
supporting information, (2021/12/23)
The addition of simple silylamines to dialkyl acetylenecarboxylates was investigated yielding both E and Z-silylenamines in contrast to an earlier report. Silylamination was also achieved with propiolates, expanding the scope of the silylamination reactio
Thermal Reactions of 6-Methyl-5--2,4(1H,3H)-pyrimidinediones with Electron-Deficient Olefins and Acetylene
Noguchi, Michihiko,Kiriki, Yasutoshi,Tsuruoka, Takashi,Mizui, Takahiro,Kajigaeshi, Shoji
, p. 99 - 105 (2007/10/02)
The thermal reactions of some 6-methyl-5--2,4(1H,3H)-pyrimidinediones (1) were investigated.The 1,5-hydrogen shift in 1 gave 5,6-dihydro-5,6-bis(methylene)-2,4(1H,3H)-pyrimidinedione intermediates, while the 1,2-hydrogen shi
The reaction of simple dimethylallylamines with dimethyl acetylenedicarboxylate. Formation of 1-dimethylamino-2-allylmaleates via formal allyl transfer
Schwan, Adrian L.,Warkentin, John
, p. 1686 - 1694 (2007/10/02)
Tertiary amines bearing two methyl groups and an allylic substituent (X) raect with dimethyl acetylenedicarboxylate (DMAD) to afford the corresponding 1-dimethylamino-2-X' maleates, in which X' is the allylic isomer of X.The mechanism postulated involves reversible formation of a zwitterion by attack of the amine at an sp-carbon of DMAD.The zwitterion then undergoes intramolecular allyl transfer, through a 6-membered transition state.Evidence for a zwitterionic intermediate (quaternary ammonium allenolate) includes capture of the allenolate centre by intramolecular addition to a carbonyl group and by proton transfer from chloroform.