Reactions of Peracids. IV. The Reaction of Cyclohexylphenyl Ketone with Perbenzoic Acid

Friess, S.L.; Farnham, N.

doi:10.1021/ja01168a042

Cited by 39 publications

(10 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The Baeyer–Villiger (B–V) oxidation reaction involving the transformation of ketones into the corresponding esters or lactones, was first reported by Baeyer and Villiger in 1899. , Subsequently, the reaction is widely used in organic synthesis, such as, synthesis of steroids and antibiotics in the field of pharmaceuticals, pheromones for agrochemistry, monomers of polymerization, etc . The B–V oxidation is traditionally carried out in noncatalytic ways using peracids oxidants including perbenzoic acid, m -chloro perbenzoic acid, trifluoroperacetic acid, etc. in more than stoichiometric quantities in complex solutions.…”

Section: Introductionmentioning

confidence: 99%

Postsynthesis and Effective Baeyer–Villiger Oxidation Properties of Hierarchical FAU-type Stannosilicate

Zhu

Jiang

et al. 2016

J. Phys. Chem. C

View full text Add to dashboard Cite

Sn−Y zeolite, with hierarchical pore systems and extremely low Al content, was successfully prepared via a convenient postsynthetic route which involves proper predealumination and subsequent (NH 4 ) 2 SnCl 6 treatment under mild aqueous condition. The Sn ions were incorporated into the framework of properly dealuminated Y zeolite through reacting with the defect sites generated in the industrial steaming treatment, the first-step acid treatment, and the second Sn incorporation process under acidic conditions. The acidic medium achieved by adding HCl in the Sn incorporation process affected not only the amount of incorporated Sn and residual Al but also the coordination state of inserted Sn ions. Compared with hydrothermally synthesized Sn-Beta, postsynthesized Sn− Y zeolite exhibited outstanding catalytic performances in the Baeyer−Villiger oxidation reactions of ketones especially when bulky tert-butyl hydroperoxide was employed as the oxidant due to an open pore structure of 3-dimensional 12-membered ring (12-MR) channels of FAU topology as well as the dealumination-derived intracrystal mesoporosity. Moreover, alkali metal ions modification was shown to be an effective approach for enhancing the selectivity of lactones.

show abstract

Section: Introductionmentioning

confidence: 99%

Postsynthesis and Effective Baeyer–Villiger Oxidation Properties of Hierarchical FAU-type Stannosilicate

Zhu

Jiang

et al. 2016

J. Phys. Chem. C

View full text Add to dashboard Cite

show abstract

“…The B-V reactions is commonly performed utilizing peracids as oxidants, including trifluoroperacetic acid [6], perbenzoic acid [7], m-chloroperbenzoic acid [2]. However, these oxidants not only contain low effective oxygen contents [8], but also are potentially explosive [9].…”

Section: Introductionmentioning

confidence: 99%

Hydrothermal synthesis of MWW-type stannosilicate and its post-structural transformation to MCM-56 analogue

Liu

Jiang

Yang

et al. 2013

Microporous and Mesoporous Materials

View full text Add to dashboard Cite

“…With peracetic acid this afkords the lactone ~vith the lower ~lleltiilg point. The Baeyer-Villiger reaction proceeds with retention of configuration of migrating optic<dly active groups (5, 6) and almost always, as in the present case, involves the migration of tlle more alliylated of the tu-o carbon atoms fla~lkiilg the carbonyl group (7,8). …”

mentioning

confidence: 50%

Stereochemical Studies: Ii. Configurations of Some 4-Oxacholestanes

Edward¹,

Morand²

1960

Can. J. Chem.

View full text Add to dashboard Cite

The oxidation of A-nor-58-cholestan-3-one with peracids gave 4-osa-58-cholestan-3-one. This was identical with one of the two lactones produced by the reductiorl of \Vindausl lceto acid: the other lactone must be 4-oxa-5a-cholestan-3-one. The two lactones were reduced by lithiulll aluminum hydride to diols, which were cyclized to 4-oxa-5a-and -58-cholestane.Turner (1) obtained by catalytic 1-eductiol~ of Winclaus' lceto acid (I) (2) two Iactones, 1n.p. 109.5°-1100 C and 11G0-11B.50 C, the foriner in larger a~n o u n t . I-Ie tentatively assigned to these compounds the structures V and VI, rcspcctively, because of their optical rotations and because hg~drogenation ot 4-osacholest-3-e1~-3-01~c, which should be expected to give VI, gave the highel-~nelting T ' ~s o~n e r .Further evidence for these structures comes from a con side ratio^^ of thcir nlolecular rotations (3) including the cliffercnces between the molecular rotations of the lactones ancl oi the amides (I1 or 111, It = K I I J or hydrazicles (I1 or 111, R = i' i\;I-1x1-I?), which are, CIS s h o~~ 11 in Table I , in the directions preclicted by the IClyne-I-Iudson "lactone rule" (3). Finally, unequivocal proof comes froin the Baeyer-Villiger oxidation of Windaus norlcetone (IV), which is lino~vn t o have the cis ring juncture shown (4). With peracetic acid this afkords the lactone ~vith the lower ~lleltiilg point. The Baeyer-Villiger reaction proceeds with retention of configuration of migrating optic

show abstract

Reactions of Peracids. IV. The Reaction of Cyclohexylphenyl Ketone with Perbenzoic Acid

Cited by 39 publications

References 0 publications

Postsynthesis and Effective Baeyer–Villiger Oxidation Properties of Hierarchical FAU-type Stannosilicate

Postsynthesis and Effective Baeyer–Villiger Oxidation Properties of Hierarchical FAU-type Stannosilicate

Hydrothermal synthesis of MWW-type stannosilicate and its post-structural transformation to MCM-56 analogue

Stereochemical Studies: Ii. Configurations of Some 4-Oxacholestanes

Contact Info

Product

Resources

About