90247-81-7Relevant academic research and scientific papers
Synthesis of benzannulated heterocycles by twofold Suzuki-Miyaura couplings of cyclic diarylborinic acids
Dimitrijevic, Elena,Cusimano, Madeline,Taylor, Mark S.
supporting information, p. 1391 - 1394 (2014/03/21)
Two-fold Suzuki-Miyaura cross-couplings of cyclic diarylborinic acids are described. This novel annulation method enables the synthesis of benzo-fused heterocycles from dihaloarenes or gem-dibromoolefins.
Reactions of enantiopure cyclic diols with sulfuryl chloride
Boyd, Derek R.,Sharma, Narain D.,Kaik, Magdalena,McIntyre, Peter B.A.,Malone, John F.,Stevenson, Paul J.
, p. 2128 - 2136 (2014/03/21)
Monocyclic allylic cis-1,2-diols reacted with sulfuryl chloride at 0 °C in a regio- and stereo-selective manner to give 2-chloro-1-sulfochloridates, which were hydrolysed to yield the corresponding trans-1,2-chlorohydrins. At -78 °C, with very slow addition of sulfuryl chloride, cyclic sulfates were formed in good yields, proved to be very reactive with nucleophiles and rapidly decomposed on attempted storage. Reaction of a cyclic sulfate with sodium azide yielded a trans-azidohydrin without evidence of allylic rearrangement occurring. An enantiopure bicyclic cis-1,2-diol reacted with sulfuryl chloride to give, exclusively, a trans-1,2-dichloride enantiomer with retention of configuration at the benzylic centre and inversion at the non-benzylic centre; a mechanism is presented to rationalise the observation.
