6048-83-5Relevant academic research and scientific papers
Acid-catalyzed transannular cyclization of medium ring unsaturated sulfides. The effect of ring size and double bond geometry on rate
Cere, Vanda,Peri, Francesca,Pollicino, Salvatore,Antonio, Arcelli
, p. 977 - 979 (2007/10/03)
The acid-catalyzed transannular cyclization of 8-10-membered γ,δ-unsaturated cyclic sulfides yields in cis fused bicyclic sulfonium salts independently of the geometry of the double bond. The rate varies linearly with the acidity function -(H0)I with a slope of 1. The rate variations span about six powers of ten range, the maximum rate difference being observed for the E/Z thiacyclooct-4-ene pair. The data are consistent with the classical interpretation of the intramolecular reactivity in terms of internal strain of the substrate and/or of the transition state.
The macrocyclization reaction of terminal dibromoalkanes with sulfide on alumina. The use of a solid support as an alternative to the high dilution technique
Tan,Pagni,Kabalka,Hillmeyer,Woosley
, p. 7709 - 7712 (2007/10/02)
The reaction of a series of terminal dibromoalkanes with S-2 on Al2O3 has been examined. The use of a solid support for the macrocyclization represents a viable alternate procedure to the more traditional high dilution technique in solution. The cyclization also occur with thioacetamide on unactivated alumina.
