Polymeric reagents. IV. Synthesis and utilization of an insoluble polymeric organotin dihydride reagent

Weinshenker, Ned M.; Crosby, Guy A.; Wong, Jack Y.

doi:10.1021/jo00901a020

Cited by 86 publications

(42 citation statements)

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“…We were somewhat concerned that our lithiation procedure might thus give more meta lithiated polymer than the prior two step procedure of bromination and lithiation and that this difference might give different results in a synthetic scheme. Because of this we made 2 by the two step procedure of Camps et al (19,20) and prepared l,l0-decanediol monoacetate on this polymer according to Scheme 2. The results were very comparable as shown in Table 1.…”

Section: Other Experimentsmentioning

confidence: 99%

“…Cross-linked polystyrene 1 was brominated as previously described (19) to give a polymer containing 26.79% Br by elemental analysis which corresponds to 3.32 mmol Br/g of polymer.…”

Section: Cm-i (C=o) Preparation Of Triply-attacired Polymer-bound Trmentioning

confidence: 99%

“…The direct lithiation of the 20% cross-linked polymer was sluggish, requiring 2 days reaction time. Although subsequent formation of a 20% crosslinked polymer-bound 4,4'-dimethoxytrityl chloride polymer was readily achieved, followed by (19). Drying the polymer under high vacuum divides the large beads giving 'split peas'.…”

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confidence: 99%

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The use of polymer supports in organic synthesis. V. The preparation of monoacetates of symmetrical diols

Fyles¹,

Leznoff²

1976

Can. J. Chem.

128

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. 54, 935 (1976). A 2% cross-linked divinylbenzene-styrene copolymer was directly lithiated with n-butyllithium in the presence of N,N,N',N1-tetramethylethylenediamine. The lithiated polymer on reaction with a benzophenone gave an insoluble polymer-bound trityl alcohol. Further reaction with acetyl chloride gave a polymer-bound trityl chloride which, on treatment with the primary symmetrical diols 1,lO-decanediol, 1,7-heptanediol, and l,rlbutanediol, gave mostly syrnmetrical diols monoblocked by insoluble polymer-bound trityl groups. Acetylation followed by acid cleavage from the polymer gave the monoacetates of 1,lO-decanediol, 1,7-heptanediol, and 1,rlbutanediol and some recovered diols. The recovered polymer can be efficiently recycled. The quantity of recovered diol was related to the problem of 'double-binding' of the symmetrical diols to the polymer-bound trityl groups. The extent of 'double-binding' could be greatly reduced by the use of polymer-bound trityl chloride prepared via the lithiated polymer and methyl benzoate or phosgene. [Traduit par le journal]

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Section: Other Experimentsmentioning

confidence: 99%

“…Cross-linked polystyrene 1 was brominated as previously described (19) to give a polymer containing 26.79% Br by elemental analysis which corresponds to 3.32 mmol Br/g of polymer.…”

Section: Cm-i (C=o) Preparation Of Triply-attacired Polymer-bound Trmentioning

confidence: 99%

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The use of polymer supports in organic synthesis. V. The preparation of monoacetates of symmetrical diols

Fyles¹,

Leznoff²

1976

Can. J. Chem.

128

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“…Bromination of microporous resins in the presence of a Lewis acid catalyst is generally carried out in the dark, whereby the loading degree can be conveniently controlled by the amount of bromine used in the reaction [74]. Macroreticular resins can be brominated using Br 2 and FeCl 3 [39], or by using a stoichiometric amount of thallium acetate as Lewis acid catalyst (Scheme 28.15) [76,77].…”

Section: Other Functionalized Polystyrene Resinsmentioning

confidence: 99%

“…For higher loadings, the bromination-lithiation route needs to be used. Lithiated polystyrene is a very versatile intermediate, since many differently functionalized polystyrene-derived resins can be obtained through different chemical reactions [76,78,80]. Scheme 28.16 shows several examples.…”

Section: Other Functionalized Polystyrene Resinsmentioning

confidence: 99%

Solid Phase and Combinatorial Chemistry in the Heterocyclic Field

Villalgordo¹

2011

Modern Heterocyclic Chemistry

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Prostaglandins

Collins¹

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Prostaglandins are a family of naturally occurring substances found in animals and humans. They are produced from 20 carbon fatty acids in vivo and play important and diverse roles in both health and disease. Unlike circulating hormones, prostaglandins are synthesized and released by most tissues, act near their site of synthesis, and then are rapidly inactivated by metabolic enzymes. They are among the most potent substances known and exert regulatory influences on virtually all tissues and organs. Because of their diverse biological effects and their potential as therapeutic agents, prostaglandins underwent intense scrutiny following their structural elucidation and availability in the early 1960s. Both academic and industrial laboratories studied their biosynthesis, metabolism, physiological and pharmacological effects, and their chemical and physical properties. The total synthesis of prostaglandins presented formidable challenges. Because of their structural and stereochemical complexity and chemical instability, they provided a strong impetus to the development of new synthetic methodologies. The prostaglandins and many analogues are available by total synthesis and some have reached the marketplace as therapeutic agents. Examples are prostaglandin E 1 (PGE 1 ), used in cardiovascular and reproductive indications; analogues of prostaglandin F 2 α , used in estrus synchronization in farm animals; misoprostol, an analogue of PGE 1 , used in the treatment of ulcers; prostacyclin and some of its analogues, used for cardiovascular diseases; and latanoprost, used in the treatment of glaucoma.

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Polymeric reagents. IV. Synthesis and utilization of an insoluble polymeric organotin dihydride reagent

Cited by 86 publications

References 0 publications

The use of polymer supports in organic synthesis. V. The preparation of monoacetates of symmetrical diols

The use of polymer supports in organic synthesis. V. The preparation of monoacetates of symmetrical diols

Solid Phase and Combinatorial Chemistry in the Heterocyclic Field

Prostaglandins

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