New Paradigms for the Peroxy Acid Epoxidation of CC Double Bonds: The Role of the Peroxy Acid s-Trans Conformer and of the 1,2-H Transfer in the Epoxidation of Cyclic Allylic Alcohols-Reference-Cited by-同舟云学术

New Paradigms for the Peroxy Acid Epoxidation of CC Double Bonds: The Role of the Peroxy Acid s-Trans Conformer and of the 1,2-H Transfer in the Epoxidation of Cyclic Allylic Alcohols

Published:2004-09-25 Issue:22 Volume:69 Page:7479-7485
ISSN:0022-3263
Container-title:The Journal of Organic Chemistry
language:en
Short-container-title:J. Org. Chem.

Author:

Freccero Mauro¹,Gandolfi Remo¹,Sarzi-Amadè Mirko¹,Rastelli Augusto¹

Affiliation:

1. Dipartimento di Chimica Organica, Università di Pavia, Viale Taramelli 10, 27100 Pavia, Italy, and Dipartimento di Chimica, Università di Modena, Via Campi 183, 41100 Modena, Italy

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/jo048980j

Reference38 articles.

1. Role of Hydrogen Bonding in the Oxidation of Thianthrene 5-Oxide with Peroxy Acids

2. (b) According to these authors, the calculated potential energy difference between s-trans (μ = 3.11 D) and s-cis (μ = 1.43 D) performic is of 2.01 kcal/mol at the B3LYP/6-311++G(d,p) level in gas phase. Our B3LYP/6-311++G(3df,2pd) calculations led to the following results: μs-cis= 1.36 D (gas), 1.45 D (benzene), 1.51 D (CH2Cl2) and μs-trans= 3.09 D (gas), 3.38 D (benzene), 3.67 D (CH2Cl2); (Gs-trans−Gs-cis)gas= 2.48 kcal/mol, (Gs-trans−Gs-cis)benzene= 1.77 kcal/mol, (Gs-trans−Gs-cis)CH2Cl2= 0.62 kcal/mol.

3. Role of solvent in the oxidation of some organic compounds by peroxyacids

4. The s-cis form of neutral peroxy acids has always been assumed as the only reactive conformer in all theoretical studies on epoxidation reactions of both alkenes and allylic alcohols.3-5

5. On the Origin of Substrate Directing Effects in the Epoxidation of Allyl Alcohols with Peroxyformic Acid

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