Reference

The acid cleavage of triphenylvinylmercuric salts

The acid cleavage of triphenylvinylmercuric salts. Lee, Choi Chuck; Smith, Peter J. (Dep. Chem. Chem. Eng., Univ. Saskatchewan, Saskatoon, Sask., Can.). 1607-57-4 which is the cas registry number is also used here. Can. J. Chem., 54(19), 3038-40 (English) 1976. CODEN: CJCHAG. DOCUMENT TYPE: Journal CA Section: 22 (Physical Organic Chemistry) An attempted solvolytic demercuration of Ph2C:CPhHgR (I, R = OAc or Br) in HOAc in the presence of HClO4 failed to give the triphenylvinyl cation, but instead gave a high yield of Ph2C:CHPh (II). Kinetic studies showed that the formation of II from the reaction of I (R = OAc) with HClO4 in MeOH was first order with respect to the substrate and 2nd order with respect to HClO4. Mechanistic implications of these findings are discussed. .

Degenerate b-aryl rearrangements in photochemically generated triarylvinyl cations

Degenerate b-aryl rearrangements in photochemically generated triarylvinyl cations. Kitamura, Tsugio; Kobayashi, Shinjiro; Taniguchi, Hiroshi; Fiakpui, Charles Y.; Lee, Choi Chuck; Rappoport, Zvi (Fac. Eng., Kyushu Univ., Fukuoka 812, Japan). J. Org. Chem., 49(17), 3167-70 (English) 1984. CODEN: JOCEAH. ISSN: 0022-3263. DOCUMENT TYPE: Journal CA Section: 22 (Physical Organic Chemistry) Irradn. of R2C:CBrR (I; R = Ph, p-tolyl, p-anisyl) in MeOH gave vinyl ethers R2C:C(OMe)R (R as above) and the phenanthrenes. 1607-57-4 is also in the experiment. A study of [2-13C] labeled bromides showed that b-aryl rearrangement takes place in the vinyl cations R2C:CR+ Br-. Irradn. of [2-13C]-I in CF3CH2OH and anal. of the extent of scrambling from C-2 to C-1 in the trifluoroethyl vinyl ethers, R2C:C(OCH2CF3)R, showed 38, 72, and 92% rearrangement of the 13C label for I, R = Ph, p-tolyl, p-anisyl, resp. Similar rearrangement of [2-13C-]-I in MeOH resulted in no rearrangement in R2C:C(OMe)R. .