65597-69-5Relevant academic research and scientific papers
Straightforward chemoselective access to unsymmetrical dithioacetals through a thiosulfonate homologation-nucleophilic substitution sequence
Ielo, Laura,Pillari, Veronica,Gajic, Natalie,Holzer, Wolfgang,Pace, Vittorio
supporting information, p. 12395 - 12398 (2020/10/30)
A sequential C1-homologation-nucleophilic substitution tactic is presented for the preparation of rare unsymmetrical dithioacetals. The judicious selection of thiosulfonates as convenient sulfur electrophilic sources - upon the homologation event conducted on an intermediate a-halothioether - guarantees the release of the non-reactive sulfonate group, thus enabling the subsequent nucleophilic displacement with an external added thiol [(hetero)- aromatic and/or aliphatic]. Uniform high yields and excellent chemocontrol were deduced during the extensive scope study, thus documenting the versatility of the direct technique for the preparation of these unique and manipulable materials.
GAS-PHASE THERMOLYSIS OF SULFUR COMPOUNDS. PART VII. 4,6-DITHIA-1-OCTENE, 4,6-DITHIA-1,8-NONADIENE AND 4,6-DITHIA-6-PHENYL-1-HEXENE
Martin, Gonzalo,Martinez, Henry,Ortega, Heriberto,Salazar, Jose
, p. 153 - 160 (2007/10/02)
Under stirred-flow conditions, the title compounds pyrolyze to yield propene and the ethyl, allyl and benzyl dithioformates, respectively, as reaction products.The first order rate coefficients of these unimolecular decompositions followed the Arrhenius equations: 4,6-dithia-1-octene: k(sec-1) = 1010.85+/-0.18exp(-142+/-2kJ/mol RT), 4,6-dithia-1,8-nonadiene: k(sec-1) = 1010.45+/-0.34exp(-132+/-4kJ/mol RT), 4,6-dithia-6-phenyl-1-hexene: k(sec-1) = 1010.09+/-0.43exp(-130+/-5kJ/mol RT).The activation parameters are discussed in relation to those of other allyl sulfides.These suggest that a sulfur atom can stabilize the transition state to the same extent as a ?-electron system.
