4882-97-7Relevant academic research and scientific papers
Anomalous C-C bond cleavage in sulfur-centered cation radicals containing a vicinal hydroxy group
Li, Zaiguo,Kutateladze, Andrei G.
, p. 8236 - 8239 (2003)
1,3-Dithianyl cation radicals having α-hydroxy-neopentyl or similar groups in position 2, which are generated via oxidative photoinduced electron transfer, undergo anomalous fragmentation necessitating refinement of the accepted mechanism. Experimental and computational data support a rationale in which proton abstraction from the hydroxy group in the initial cation radical does not cause a Grob-like fragmentation, but rather produces a neutral radical species, the alkoxy radical, that undergoes fragmentation in either direction, i.e., cleaving the C-C bond to dithiane or to the tertiary alkyl group.
