Reaction of trimethylsilyloxy-1,3-dienes with lead(IV) benzoate

m-Chloroperbenzoic acid oxidation of 2-trimethylsilyloxy-1,3-dienes. Synthesis of .alpha.-hydroxy and .alpha.-acetoxy enones

“…This phenomenon is general for these systems, as evidenced by the reaction of 3 with Simmons-Smith reagent6 and halogen.7 It should be noted that lead(IV) benzoate, in certain cases, adds to 3 in a 1,4 manner. 8 Further, in the present work, no evidence of products arising from the oxidation of both double bonds in 3 was obtained.…”

“…The reaction of 1 with mercuric chloride gave a product which appeared to be a complex of the expected 5,7-bis-(chloromercuri) derivative11 with mercuric chloride. Reaction with 2 equiv of mercuric acetate, however, gave a 65% yield of the 5,7-diacetoxymercuri compound (8). The use of excess mercuric acetate resulted in no separation of 8 from the solution, and 8 was redissolved by the reagent, again indicating complexation.…”

Synthesis of cyclohexadienylstannanes – Novel example of vinylic SRN1 mechanism: A theoretical and experimental study

“…The method used was essentially that described by Rubottom et al [18], trapping the enolate with diethylchlorophosphate.…”

Synthetic studies on the ambiguine family of alkaloids: construction of the ABCD ring system

“…Following the protocol of Rubottom and Gruber,7 commerically available m -methylanisole was converted to 7 utilizing a Birch reduction followed by hydrolysis (Scheme 2). Secondary alcohol 7 was protected with TBSCl and imidazole, followed by treatment with vinylmagnesium bromide to afford the quaternary center substrate as the corresponding TMS-enol ether.…”