84681-15-2Relevant academic research and scientific papers
A novel multicomponent reaction of dimethoxycarbene and DMAD with aldehydes and quinones: Facile synthesis of dihydrofuran derivatives
Nair, Vijay,Bindu,Balagopal, Lakshmi
, p. 2043 - 2044 (2001)
The zwitterionic species generated by the addition of dimethoxy carbene to dimethyl acetylenedicarboxylate (DMAD) is trapped by aldehydes and quinones to yield dihydrofuran derivatives in good yields.
Novel dipolar cycloaddition reactions of zwitterionic species generated from dimethoxycarbene and dimethyl acetylenedicarboxylate with carbonyl compounds: Facile synthesis of dihydrofuran derivatives
Nair, Vijay,Bindu,Sreekumar,Balagopal, Lakshmi
, p. 1446 - 1456 (2007/10/03)
The reaction of 1:1 zwitterionic species, generated in situ by the addition of dimethoxycarbene to dimethyl acetylenedicarboxylate, towards carbonyl compounds is described. The reactions presented offer a one-pot synthesis of dihydrofuran and spiro dihydrofuran derivatives in high yields.
Selective Formation and Trapping of Dihalocarbonyl Ylides Derived from Dihalocarbenes and Substituted Benzaldehydes
Gill, Harpal S.,Landgrebe, John A.
, p. 1051 - 1055 (2007/10/02)
The thermal decompositions of several phenyl(trihalomethyl)mercury compounds in the presence of substituted benzaldehydes 1 and dimethyl acetylenedicarboxylate (7) in dry benzene at 80 deg C resulted in 2-halo-5-arylfuran-3,4-dicarboxylates 9 in isolated yields (not optimized) that ranged from 13percent to 64percent.These products appear to be the result of selective attack by dihalocarbene on the aldehyde followed by preferential capture of the resulting carbonyl ylide by the acetylenic dipolarophile and loss of hydrogen halide.The substitution of diethyl fumarate (12) for acetylene 7 produced a mixture of the E and Z isomers of dihydrofuran 14 in a ratio of 70:30.Tetrasubstituted dipolarophiles failed to give comparable products.The intermediate dihalocarbonyl ylides were shown to undergo halogen exchange.
