872-98-0Relevant articles and documents
Synthesis and bactericidal activity of substituted cyclic acetals
Tugarova,Kazakova,Kamnev,Zlotskii
, p. 1930 - 1933 (2015/02/02)
A series of substituted cyclic acetals were synthesized and tested for their bactericidal activity against bacteria strain Azospirillum brasilense Sp245.
Acetolysis of Cyclic Acetals: Regioselective Acylative Cleavage of Cyclic Formals
Bailey, William F.,Rivera, Alberto D.
, p. 4958 - 4964 (2007/10/02)
The acid-catalyzed reaction of cyclic acetals with acetic anhydride has been investigated.Acylative cleavage of cyclic formals has been found to be a clean, high-yield reaction involving rupture of the C(2)-O bond with loss of stereochemical integrity at the C(2)-position to give hemiacetal acetate products.Ring cleavage of unsymmetrically substituted cyclic formals with either acetic anhydride or acetyl chloride occurs via preferential rupture of the less congested C(2)-O bond (Scheme I, path A).Such cleavage is totally regiospecific for 1,3-dioxanes and displays high (75-85percent) regioselectivity for smaller and larger ring systems.Acetolysis of cyclic acetals other than formals is a slow process that leads to loss of the aldehyde derived fragment and formation of simple diacetates.These results are rationalized in terms of rate-limiting electrophilic attack that is acutely sensitive to steric effects engendered by substituents located at positions adjacent to ring oxygens.
Elimination, Fragmentation, and Proton Transfer in 1,3-Dithianes and 1,3-Dithiolanes in the Gas Phase
Bartmess, John E.,Hays, Robert L.,Khatri, Hiralal N.,Misra, Raj N.,Wilson, Stephen R.
, p. 4746 - 4751 (2007/10/02)
The gas-phase negative ion-molecule chemistry of 1,3-dithianes and 1,3-dithiolanes differs considerably from the in solution.When treated with anionic bases, 1,3-dithiane undergoes successive elimination reactions giving thiolates, in competition with deprotonation at the 2-carbon, which is the sole solution phase reaction channel.The appearence of the various product ions with changing base strength agrees with their calculated thermochemical onset.The gase-phase acidity of 1,3-dithiane is measurable if the elimination reaction is blocked by gem-dimethyl substitution at the 5 carbon.For 1,3-dithiolane, no deprotonation product is pbserved; even at thermochemical treshold, cycloreversion to RCS2- and ethylene occurs.This competes with successive elimination to thiolates, as with the six-membered ring.The differences between the gas phase and solution reactivities are rationalized in terms of counterion effects.
