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The chalcogeno-Baylis-Hillman reaction: a new preparation of allylic alcohols from aldehydes and electron-deficient alkenes

✍ Scribed by Tadashi Kataoka; Tetsuo Iwama; Shin-ichiro Tsujiyama; Tatsunori Iwamura; Shin-ichi Watanabe

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
841 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

The chalcogeno-Baylis-Hillman reaction catalyzed by sulfides and selenides, the group 16 element compounds, in the presence of Lewis acids was developed. The reactions proceeded smoothly by the use of 1 equiv of Tic14 to give the coupling products in moderate to good yields.

Bischalcogenides and related compounds were investigated as a catalyst, and 1.5diselenocyclooctane gave the best result owing to stabilization of a cationic intermediate by the transannular interaction.

📜 SIMILAR VOLUMES

ChemInform Abstract: Reexamination of Pr
ChemInform Abstract: Reexamination of Products and the Reaction Mechanism of the Chalcogeno-Baylis—Hillman Reaction: Chalcogenide—TiCl4-Mediated Reactions of Electron-Deficient Alkenes with Aldehydes.
✍ Tadashi Kataoka; Hironori Kinoshita; Tetsuo Iwama; Shin-ichiro Tsujiyama; Tatsun 📂 Article 📅 2000 🏛 John Wiley and Sons ⚖ 33 KB 👁 1 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

Imidazole-catalysed Baylis–Hillman react
Imidazole-catalysed Baylis–Hillman reactions: a new route to allylic alcohols from aldehydes and cyclic enones
✍ Rafik Gatri; Mohamed Moncef El Gaı̈ed 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 58 KB

An efficient one-pot synthesis of cyclic Baylis-Hillman adducts is described. An imidazole-catalysed coupling reaction between cyclic enones and both aliphatic and aromatic aldehydes leads to allylic alcohols in moderate to good yields.

Studies on Novel Synthetic Methodologies
Studies on Novel Synthetic Methodologies. Part 51. Hypervalent Iodine-Mediated Interaction of Aldoximes with Activated Alkenes Including Baylis—Hillman Adducts: A New and Efficient Method for the Preparation of Nitrile Oxides from Aldoximes.
✍ Biswanath Das; Harish Holla; Gurram Mahender; Joydeep Banerjee; Majjigapu Ravind 📂 Article 📅 2005 🏛 John Wiley and Sons ⚖ 143 KB 👁 2 views

## Abstract For Abstract see ChemInform Abstract in Full Text.