72814-47-2Relevant academic research and scientific papers
Attempted Simmons-Smith reaction on α-oxoketene dithioacetals: A new general route to 3,4-substituted and annelated thiopenes
Bhat,Thomas,Ila,Junjappa
, p. 10377 - 10388 (2007/10/02)
A new general synthesis of 3- and 3,4-substituted 4a-q, 3,4-annelated 7a-d and condensed tricyclic 9a-e thiophenes has been developed through Simmons-Smith reaction of the respective α-oxoketene dithioacetals. Extension of the reaction of α-cinnamoylketene dithioacetals 10a-e and its higher enyl analogs 13a-d, 15a-c gave the corresponding 3-styryl 11a-e and 3-di- and trienyl 14a-d, 16a-c thiophenes in highly regioselective manner. A probable mechanism involving an unusual intramolecular aldol condensation of sulphonium ylid formed through carbenoid methylene insertion on divalent sulfur has been suggested.
ATTEMPTED SIMMONS-SMITH REACTION ON α-OXOKETENE DITHIOACETALS: A NEW GENERAL ROUTE TO 3,4-SUBSTITUTED AND ANNELATED THIOPHENES
Thomas, Abraham,Singh, Gurdeep,Ila, Hiriyakkanavar,Junjappa, Hiriyakkanavar
, p. 3093 - 3096 (2007/10/02)
A new general method for 3,4-substituted and annelated thiophenes through intramolecular cyclocondensation of a sulphonium ylid intermediate under Simmons-Smith reaction conditions on α-oxoketene dithioacetals has been reported.
