✦ LIBER ✦

Reaction of an ammonium eneselenolate derived from a selenothioacetic acid S-ester with electron-deficient alkenes and alkynes

✍ Scribed by Toshiaki Murai; Taichi Kondo; Shinzi Kato

Publisher: John Wiley and Sons
Year: 2004
Tongue: English
Weight: 108 KB
Volume: 15
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.20003

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Ammonium eneselenolate 2 derived from selenothioic acid S‐ester 1 was reacted with electron‐deficient alkenes 4 and alkynes 9. Ammonium eneselenolate 2 underwent Michael addition with 4 to give two types of Michael adducts, 5 and 6. Products 6 incorporated two molecules of 4. In contrast, the reaction of 2 with 9 took place at the selenium atom to give γ‐oxo divinyl selenides 10 with high Z‐stereoselectivity. During the further elaboration of the reactivity of the products derived from 2 and carbonyl compounds, unexpected reaction was found in the addition of vinylmagnesium bromide to Se‐vinyl ester 3. The spectroscopic data supported the formation of the enol form 12 of β‐oxo selenothioic acid S‐ester 13. © 2004 Wiley Periodicals, Inc. Heteroatom Chem 15:187–192, 2004; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20003

📜 SIMILAR VOLUMES

Reaction of an Ammonium Eneselenolate De

Reaction of an Ammonium Eneselenolate Derived from a Selenothioacetic Acid S-Ester with Electron-Deficient Alkenes and Alkynes.

✍ Toshiaki Murai; Taichi Kondo; Shinzi Kato 📂 Article 📅 2004 🏛 John Wiley and Sons ⚖ 123 KB 👁 2 views

ChemInform Abstract: Cycloaddition React

ChemInform Abstract: Cycloaddition Reaction of 2-Azadienes Derived from β-Amino Acids with Electron-Rich and Electron-Deficient Alkenes and Carbonyl Compounds. Synthesis of Pyridine and 1,3-Oxazine Derivatives.

✍ Francisco Palacios; Esther Herran; Gloria Rubiales; Jose Maria Ezpeleta 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 40 KB 👁 1 views

ChemInform Abstract: An Efficient Synthe

ChemInform Abstract: An Efficient Synthesis of Aryldithiocarbamic Acid Esters from Michael Addition of Electron-Deficient Alkenes with Arylamines and CS2 in Solid Media Alkaline Al2O3.

✍ Shuai Xia; Xin Wang; Ze-mei Ge; Tie-ming Cheng; Run-tao Li 📂 Article 📅 2009 🏛 John Wiley and Sons ⚖ 37 KB 👁 1 views

ChemInform Abstract: Orthogonal Synthesi

ChemInform Abstract: Orthogonal Synthesis of Densely Functionalized Pyrroles and Thiophenes from the Reactions of Imidazo[1,5-a]pyridine Carbene-Derived Zwitterions with Electron-Deficient Alkynes.

✍ Ying Cheng; Jiang-Hua Peng; Jia-Qi Li 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 37 KB 👁 2 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

ChemInform Abstract: Lewis Acid Promoted

ChemInform Abstract: Lewis Acid Promoted Hetero [2 + 2] Cycloaddition Reactions of Aldehydes with 10-Propynyl-9(10H)-acridone. A Highly Stereoselective Synthesis of Acrylic Acid Derivatives and 1,3-Dienes Using an Electron Deficient Variant of Ynamine.

✍ Richard P. Hsung; Craig A. Zificsak; Lin-Li Wei; Christopher J. Douglas; Hui Xio 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 35 KB 👁 2 views