By S. Sundaram, P.S. Raghavan (auth.)
ISBN-10: 3642208169
ISBN-13: 9783642208164
Chromic acid and chromium oxide are the 2 flexible Cr(VI) oxidants recognized to natural chemists for many years. The creation of the Core's reagent , viz: pyridinium chlorochromate, in 1975 through the guides on numerous Cr(VI) oxidizing brokers containing the -onium chromates and halochromates within the final 3 many years have greatly replaced the chemistry of oxidations with Chromium VI. a number of of those new reagents were proven to be gentle so we can be dealt with simply and the reacton items can also be managed. a few of them are hugely selective oxidants for positions like allylic hydroxylic staff, etc., and a few different are hugely regioselective. the knowledge on greater than 36 such reagents said in a variety of across the world reputed journals spanning approximately 280 references were gathered and supplied during this ebook in this sort of demeanour that it'll be very valuable for execs, researchers, lecturers and graduate scholars operating in natural synthesis.
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Additional info for Chromium -VI Reagents: Synthetic Applications
Example text
Thus K2Cr2O7 in either DMSO or PEG-400 brings about a specific oxidation of the allylic and benzylic alcohols; the saturated alcohols are not at all affected. 4). Bis (tetra-n-butylammonium) dichromate is also specific for allylic and benzylic alcohols while unactivated alcohols resist attack by this reagent [1]. Chromyl chloride has been well known [50, 51] since the discovery of Etard’s reaction as one of the best reagents to yield aldehyde from substituted aromatic hydrocarbons. Nalliah and Strickson have reported [52] that the Etard adducts of aromatic primary amines with CrO2Cl2 in CCl4 or CHCl3 on hydrolysis result in the formation of a mixture of azobenzenes, 1,4-benzoquinones, 1,4-benzoquinone anils and aniline-1,4-benzoquinone.
34. 35. 36. 37. 38. 39. Narayanan N, Balasubramanian TR (1986) Indian J Chem 25B:228 Firouzabadi H, Sardarian A, Gharibi H (1984) Synth Commun 14:89 Ruggero Curci, Luigi Lopez, Luigins Troisi (1988) Tetrahedron Lett 29(25):3145 Santanielo E, Milani F, Casati R (1983) Synthesis 749 Gun LeeJong, Soo HaDong, Jong LimHee (1988) Bull Korean Chem Soc 9B:407 Harry DB, Roger SM, Jeanne BM, William PW (1983) Heterocycles 20:2029 Frank S Guziec Jr, Frederick A Luzzio (1980) Synthesis 691 Bhattacharjee MN, Chaudhui MK, Dasgupta HS, Roy N, Khathing DT (1982) Synthesis 588 Frechet Jean MJ, Darling P, Farrall Jean MJ (1981) Org Chem 46:1728 Santaniello E, Ferraboschi P, Sozzani P (1980) Synthesis 646 Balasubramanian K, Prathiba V (1986) Indian J Chem 25B:326 Lopez CM, Gonzalez A, Cossio FP, Palomo C (1985) Synth Commun 15:1197 Corey EJ, Suggs JW (1975) Tetrahedron Lett 2647 Tang M, Huang X, Chen Z, Hangzhou daxue X (1984) Ziran Kexucban 11(4):454.
NH O – + O O – Cr O – Cl O+ (4) The presence of fluoride ion has also been reported [84] to facilitate the cleavage of Si–O bonds by Jone’sreagent. Thus the addition of KF to Jone’s reagent enabled it to oxidize t-butyldimethylsilyl and trimethylsilyl ethers in 98% yield just in 1 h at 0 °C in acetone to the respective ketones or carboxylic acids. However, t-butyl diphenyl silyl ether resists oxidation under similar conditions. In contrast to such augmentations of oxidation potency of Cr(VI) reagents by auxiallary reagents, Corey et al.
Chromium -VI Reagents: Synthetic Applications by S. Sundaram, P.S. Raghavan (auth.)
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