𝔖 Bobbio Scriptorium
✦   LIBER   ✦

The Reaction of Singlet Oxygen with 1,3-Dimethylindole in the Presence of Aldehydes. Formation of 1,2,4-Trioxanes

✍ Scribed by Charles W. Jefford; Danielle Jaggi; John Boukouvalas; Shigeo Kohmoto; Gérald Bernardinelli

Publisher
John Wiley and Sons
Year
1984
Tongue
German
Weight
441 KB
Volume
67
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The dye‐sensitized photo‐oxygenation of 1,3‐dimethylindole in the presence of aldehydes initially generates a zwitterionic peroxide which condenses with the carbonyl function to give the corresponding cis‐fused 1,2,4‐trioxanes. Acetaldehyde gives a pair of diastereomers, one of whose structures was determined by X‐ray analysis (cis,__cis__isomer), whereas pivaladehyde gives only the cis,cis diastereomer.

📜 SIMILAR VOLUMES

The Reaction of Biadamantylidene with Si
The Reaction of Biadamantylidene with Singlet Oxygen in the Presence of Dyes [1]
✍ Charles W. Jefford; André F. Boschung 📂 Article 📅 1977 🏛 John Wiley and Sons 🌐 German ⚖ 646 KB

## Abstract Singlet oxygen, generated chemically or photogenetically, reacts with biadamantylidene to give the corresponding dioxetane and epoxide only. When methylene blue (MB) or __meso__‐tetraphenylporphin (__m__‐TPP) is used as sensitizer the normal reaction course occurs giving dioxetane as th

The Diastereoselective Formation of 1,2,
The Diastereoselective Formation of 1,2,4-Trioxanes and 1,3-Dioxolanes by the reaction of endoperoxides with chiral cyclohexanones
✍ Charles W. Jefford; Shu-Juan Jin; Gérald Bernardinelli 📂 Article 📅 1997 🏛 John Wiley and Sons 🌐 German ⚖ 963 KB

Dedicated to Professor Dieter Seebach on the occasion of his 60th birthday (26. VI.97) 1,4-Diphenyl-2,3-dioxabicyclo[2.2.l]hept-5-ene (2), on treatment with a catalytic amount of trimethylsilyl trifluoromethanesulfonate (Me,SiOTf) in CH,CI, at -78", reacts with excess (-)-menthone (10) to give (1 S,