Ring Expansion or Spirocyclisation of (Phenylthiomethylene)cycloalkanes with Aluminium Chloride via β-Thio Carbocations
The title reactions can be explained by Wagner-Meerwein rearrangement of α-thio carbocations (thionium ions) to β-thio carbocations; this unusual reactivity may be due to superelectrophilic activation by aluminium chloride.
Derouane, Daphne,Harvey, Jeremy N.,Viehe, Heinz G.
Addition of C6H5SCl to alkenes 8, 10, and 14 yields allyl thioethers 9, 11, and 15 + 16 after thermolysis at 120 - 200 deg C.Vinyl thioethers are not observed.The influence of substituents R1 and R2 on the regioselectivity (Table 1) and the rate of the elimination (Table 2) is examined.
Giese, Bernd,Mazumdar, Pronab
p. 2859 - 2865
(2007/10/02)
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