Get Comprehensive Organic Functional Group Transformations II: PDF

By Alan R. Katritzky, Richard J. K. Taylor and Gary Molander

ISBN-10: 0080442552

ISBN-13: 9780080442556

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By Alan R. Katritzky, Richard J. K. Taylor and Gary Molander

ISBN-10: 0080442552

ISBN-13: 9780080442556

Show description

Read Online or Download Comprehensive Organic Functional Group Transformations II: v. 4(Carbon with Two Heteroatoms, Each Attached by a Single Bond) PDF

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Additional info for Comprehensive Organic Functional Group Transformations II: v. 4(Carbon with Two Heteroatoms, Each Attached by a Single Bond)

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Org. Chem. 1999, 64, 3398–3408. K. Uneyama, G. Mizutani, K. Maeda, T. Kato, J. Org. Chem. 1999, 64, 6717. G. S. Lal, G. P. Pez, R. J. Pesaresi, F. M. Prozonic, H. Cheng, J. Org. Chem. 1999, 64, 7048–7054. G. W. Kabalka, N. S. Li, S. Yu, J. Organomet. Chem. 1999, 572, 31–36. E. -P. Paugam, M. -Y. Ne´de´lec, Synt. Commun. 1999, 29, 4015–4024. J. P. -L. Wang, Synth. Commun. 1999, 29, 4101–4112. R. C. Mebane, K. M. Smith, D. R. Rucker, M. P. Foster, Tetrahedron Lett. 1999, 40, 1459–1462. M. Kirihara, T.

In this way the phenoxide anion derived from 25 (Equation (14)) affords the -fluoroether 26 <2000JFC(105)129>. The regiochemistry of the addition to trifluorovinyl ethers is controlled not only by the inductive effect of the fluorine substituents but also by the stabilization of the intermediate carbanion by negative hyperconjugation . The perfluoroalkyl vinyl ether 27 is easily synthesized <2000JFC(106)13> and is also commercially available, and so has been used as a model compound in a number of studies of this type of addition reaction (Table 2).

The electrochemical fluorination of a number of esters carrying morpholine substituents leads to the formation of mixtures of products, which include a number of -fluoroethers <1998JFC(87)193, 2001JFC(111)115>. Thus, methyl cis-dimethylmorpholinopropionate gives a product mixture which contains the -fluoroethers 18 and 19 (Equation (10)), and methyl cis-dimethylmorpholinoacetate, in addition to the corresponding acid fluoride (47%) and N-perfluoroalkyl deivative (2%), gives a small amount of the oxazepan 20.

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Comprehensive Organic Functional Group Transformations II: v. 4(Carbon with Two Heteroatoms, Each Attached by a Single Bond) by Alan R. Katritzky, Richard J. K. Taylor and Gary Molander


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