Investigation of Chemical Properties and Antimicrobial Activity of Acetylene Glycidyl Ethers

A Computational Study of 2-(chloromethyl)oxirane Ring Opening by Bromide and Acetate Anions Considering Electrophilic Activation with Cations of Alkali Metals

“…[1][2][3] The ring opening of the substituted oxiranes leads to a parallel formation of normal (n-P) and abnormal (a-P) products (Scheme 1), which are versatile intermediates in organic synthesis due to three reaction centers at contiguous carbon atoms. [4][5][6][7][8] Only normal product transformations allow obtaining the glycidyl esters, which are important compounds for polymer industry. [4][5][6][8][9][10] According to the Krasusky rule, [11] the formation of the n-P esters is favored [12][13][14] and is in good agreement with nucleophilic attack through SN2 mechanism with some contribution of "borderline" SN2-like mechanism.…”

“…[4][5][6][7][8] Only normal product transformations allow obtaining the glycidyl esters, which are important compounds for polymer industry. [4][5][6][8][9][10] According to the Krasusky rule, [11] the formation of the n-P esters is favored [12][13][14] and is in good agreement with nucleophilic attack through SN2 mechanism with some contribution of "borderline" SN2-like mechanism. [15] Scheme 1 exhibits the possible directions of attack by a nucleophilic reagent on both carbon atoms of the oxirane ring of 2-(chloromethyl)oxirane (epichlorohydrin, R Scheme 1.…”

Copper-Catalyzed Oxyalkynylation of C–S Bonds in Thiiranes and Thiethanes with Hypervalent Iodine Reagents

“…The obtained β-hydroxy sulfide motif is found in a large array of bioactive molecules and is mostly accessed by epoxide ring opening. The reverse approach exploiting thiirane chemistry has been less developed, except for the acetolysis of carbohydrate bearing a thiirane at the C 5 –C 6 position …”