An-Additions to 2,5-dimethoxy-2,5-dihydrofurans, containing electron-accepting substituents in position 3

1982 ◽  
Vol 47 (11) ◽  
pp. 3055-3061 ◽  
Author(s):  
Ivan Stibor ◽  
Jan Šrogl ◽  
Miroslav Janda ◽  
Naděžda Piričová ◽  
Karel Vlažný

3-Acetyl-2,5-dimethoxy-2,5-dihydrofuran (V) was alkylated in position 4 with lithium dimethylcuprate and lithium dibutylcuprate. The reaction, proceeding with loss of methanol, afforded 4-acetyl-3-methyl-2-methoxy-2,3-dihydrofuran (X) and 4-acetyl-3-n-butyl-2-methoxy-2,3-dihydrofuran (XI), respectively. Addition of sodium salt of diethyl malonate gave 3-acetyl-4-bis(ethoxycarbonyl)methyl-2,5-dimethoxytetrahydrofuran (XVII) in 69% yield. Addition of methanol, n-butanol and tert-butyl alcohol to methyl 2,5-dimethoxy-2,5-dihydro-3-furoate (VI) in the presence of the corresponding alkoxides afforded the 4-alkoxy derivatives in 95%, 62% and 56% yield, respectively. Reaction of the compound VI with ethyl lithioacetate led to 3-ethoxycarbonylmethyl-4-methoxycarbonyl-2-methoxy-2,3-dihydrofuran (XVI) arising from the addition product by loss of methanol.


1986 ◽  
Vol 64 (6) ◽  
pp. 1060-1071 ◽  
Author(s):  
Peter James Smith ◽  
Jyotsna Pradhan

The solvolytic reaction of several 9-(ortho-substituted phenylmethyl)fluoren-9-yltrimethylammonium salts has been investigated in several different solvents. Substitution and elimination products were found for the reactions in all the solvents studied, with the exceptions that reaction in both tert-butyl alcohol and chloroform led exclusively to the alkene product. The observed rate constants for alkene formation and the percent alkene were measured and it was found that the di-ortho compounds reacted at a faster rate but produced less alkene than the reaction of the corresponding mono-ortho salts. Hydrogen–deuterium isotope effects were also determined for the various reactions. The results are discussed in terms of the reaction proceeding by way of the E1 mechanism, where steric acceleration promotes the loss of the bulky ammonium leaving group to give the carbocation intermediate.



1993 ◽  
Vol 58 (5) ◽  
pp. 1001-1006 ◽  
Author(s):  
Oľga Vollárová ◽  
Ján Benko

The kinetics of oxidation of [Co(en)2SCH2COO]+ with S2O82- was studied in water-methanol and water-tert-butyl alcohol mixtures. Changes in the reaction activation parameters ∆H≠ and ∆S≠ with varying concentration of the co-solvent depend on the kind of the latter, which points to a significant role of salvation effects. The solvation effect on the reaction is discussed based on a comparison of the transfer functions ∆Ht0, ∆St0 and ∆Gt0 for the initial and transition states with the changes in the activation parameters accompanying changes in the CO-solvent concentration. The transfer enthalpies of the reactant were obtained from calorimetric measurements.



2021 ◽  
pp. 116913
Author(s):  
Márcio José da Silva ◽  
Diego Morais Chaves ◽  
Sukarno Olavo ferreira ◽  
Rene Chagas da Silva ◽  
Jose Balena Gabriel Filho ◽  
...  




1954 ◽  
Vol 46 (6) ◽  
pp. 59-59
Author(s):  
J Westwater ◽  
L Audrieth


2008 ◽  
Vol 9 (10) ◽  
pp. 1982-1986 ◽  
Author(s):  
Yingli Wang ◽  
Lei Xu ◽  
Zhengxi Yu ◽  
Xinzhi Zhang ◽  
Zhongmin Liu


ChemInform ◽  
2010 ◽  
Vol 24 (3) ◽  
pp. no-no
Author(s):  
V. A. CHAUZOV ◽  
L. P. KOSTINA


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