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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Alkenes can be dihydroxylated using potassium permanganate.  The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
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Oxidative DMSO Cyclization Cascade to Bicyclic Hydroxyketonitriles.

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Thermolysis of iodoalkyl-siloxyalkenenitriles in DMSO initiates an oxidative cyclization cascade. This process yields highly oxygenated hydrindanones, decalones, and undecanones through an unusual, uncatalyzed reaction.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Reaction Mechanisms

Background:

  • The synthesis of complex oxygenated polycyclic compounds remains a significant challenge in organic chemistry.
  • Developing novel cyclization strategies is crucial for accessing diverse molecular architectures.

Purpose of the Study:

  • To investigate the thermolysis of ω-iodoalkyl-β-siloxyalkenenitriles in DMSO.
  • To explore the mechanism and scope of the resulting oxidative cyclization cascade.
  • To synthesize highly oxygenated hydrindanones, decalones, and undecanones.

Main Methods:

  • Thermolysis of specific ω-iodoalkyl-β-siloxyalkenenitriles in dimethyl sulfoxide (DMSO).
  • Analysis of reaction products using spectroscopic techniques.
  • Mechanistic studies to elucidate the cascade pathway.

Main Results:

  • The thermolysis triggers an unexpected oxidative cyclization cascade.
  • The cascade successfully generates highly oxygenated hydrindanones, decalones, and undecanones.
  • The reaction proceeds via an uncatalyzed enolsilyl ether crossed-aldol reaction, forming contiguous tertiary-quaternary-tertiary stereocenters.

Conclusions:

  • The described thermolysis provides a novel and efficient route to complex oxygenated polycyclic ketones.
  • The reaction highlights an unusual cascade involving an uncatalyzed aldol reaction and quaternary center equilibration.
  • This methodology offers a powerful tool for constructing intricate molecular frameworks.