Organic synthesis using a hypervalent iodine reagent: unexpected and novel domino reaction leading to spiro cyclohexadienone lactones.
نویسندگان
چکیده
The reaction of 1-(p-hydroxyaryl)cyclobutanols and phenyl iodide(III) diacetate in hexafluoroisopropanol and water produced spiro cyclohexadienone lactones via a domino reaction.
منابع مشابه
Hypervalent iodine mediated synthesis of carbamate protected p-quinone monoimine ketals and p-benzoquinone monoketals.
A simple and efficient method for the synthesis of p-quinone monoimide ketals and p-benzoquinone monoketals by using a hypervalent iodine reagent, diacetoxyiodobenzene, has been developed. These two types of ketals are achieved from a single starting material by varying the reaction conditions.
متن کاملSeven-membered rings through metal-free rearrangement mediated by hypervalent iodine.
A versatile and metal-free approach for the synthesis of carbocycles and of heterocycles bearing seven- and eight-membered rings is described. The strategy is based on ring expansion of 1-vinylcycloalkanols (or the corresponding silyl or methyl ether) mediated by the hypervalent iodine reagent HTIB (PhI(OH)OTs). Reaction conditions can be easily adjusted to give ring expansion products bearing ...
متن کاملNew synthesis of spirocycles by utilizing in situ forming hypervalent iodine species.
A very effective spirocyclization procedure for installing nucleophiles (Nu = N(3), NO(2), SCN, SO(2)Tol, and halogens) via iodonium(III) salts has been developed using the combination of iodoarene and mCPBA. The high-yielding syntheses of the cyclohexadienone-type spirocyclic compounds 2 having varied functionalities in the skeletons have been achieved from the aryl alkynes 1 with the optimize...
متن کاملThree component one-pot synthesis of 4H-benzo-[b]-pyran derivatives using [(diacetoxyiodo)benzene] (DIB) as a hypervalent iodine catalyst
The three components one pot synthesis of 2-amino-4H-benzo-[b] -pyran derivatives were obtained in good to excellent yields within short reaction time by condensing dimedone, aldehydes and malanonitrile or ethylcyanoacetate using a catalytic amount of (diacetoxyiodo)benzene as hypervalent iodine in aqueous ethanol under reflux conditions have been discussed. This aqua mediated Knoevenagel-cyclo...
متن کاملHypervalent iodine mediated oxidative amination of allenes.
An oxidative amination of allenes using a single hypervalent iodine reagent is reported. The reaction proceeds very efficiently for monosubstituted allenes and leads to formation of the corresponding propargylic amines, either as the internal or as the terminal amine. The respective reaction outcome could be influenced in favor of the former product by addition of triphenylphosphine oxide to th...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 46 23 شماره
صفحات -
تاریخ انتشار 2010