Borane adducts of selected trialkylamines with isopropyl and isobutyl groups of intermediate steric requirements have been prepared and examined as hydroborating agents. Their
reactivity toward 1-octene follows the order i-Pr2NEt·BH3 < i-Bu3N·BH3 < i-PrNBu
i
2·BH3
< i-Pr2NCH2CH2OMe·BH3 < i-Pr2NBu
i
·BH3 < i-Pr3N·BH3 < i-Pr2NBu
s
·BH3. Borane adducts
with i-Pr2NBu
i
, i-Pr3N, and i-Pr2NBu
s
are highly reactive, hydroborating 1-octene in THF
at room temperature in less than 1 h. The adduct i-Pr2NBu
i
·BH3 is a liquid above 0 °C, 4.6
M in BH3, stable over long periods, and soluble in diethyl ether, tert-butyl methyl ether,
tetrahydrofuran, dioxane, dichloromethane, and n-pentane. The adduct i-Pr3N·BH3 is a solid,
while i-Pr2NBu
s
·BH3 is a liquid, unstable, slowly evolving diborane at room temperature.
178ChemInform Abstract Methyl phenyl sulfoxide (I) is treated with trifluoroacetic anhydride (II) to generate the trifluoroacetoxysulfonium salt (III) which is employed as phenylsulfenylation reagent for the cyclic vinyl ethers (IV) or indole (VI), producing the phenyl sulfides (V) or (VII) via base-induced demethylation of the intermediate sulfonium salts.
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The p‐benzoquinonecarboxylate (II), generated in situ by treatment of the hydroquinone (I) with silver oxide, undergoes Diels‐Alder reaction with the protected trihydroxyhepta‐1,3‐dienes (III), forming the tetrahydronaphthoquinones (IV).
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