𝔖 Bobbio Scriptorium
✦   LIBER   ✦

The Reaction of Singlet and Triplet Oxygen with 2-Phenylnorbornene

✍ Scribed by Charles W. Jefford; André F. Boschung; Christian G. Rimbault

Publisher
John Wiley and Sons
Year
1976
Tongue
German
Weight
514 KB
Volume
59
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The reaction of singlet oxygen with 2‐phenylnorbornene (1) in aprotic solvents gives 3‐formylcyclopentyl phenyl ketone (2) (10%) and uncharacterized polymer (90%). When methanol is used as solvent, endo‐2‐phenyl‐exo‐2‐methoxy‐exo‐3‐hydroperoxynorbornane (4) and endo‐2‐(anti‐1′, 4′‐epidioxy‐5′,6′‐epoxycyclohex‐2′‐enyl)‐exo‐2,3‐epoxynorbornane (6 and 7) are obtained in addition to 2. Triplet oxygen with 1 gave 2, endo‐2‐phenyl‐exo‐2,3‐epoxynorbornane (8), and the trimer 9 or 10 of exo‐2,3‐epidioxy‐endo‐2‐phenylnorbornane. With protic solvents the amount of epoxide increased at the expense of trimer. The singlet and triplet oxygen reactions are discussed in the light of possible intermediates.

📜 SIMILAR VOLUMES

The Reaction of Singlet Oxygen with α- a
The Reaction of Singlet Oxygen with α- and β-Pinenes
✍ Charles W. Jefford; André F. Boschung; Robert M. Moriarty; Christian G. Rimbault 📂 Article 📅 1973 🏛 John Wiley and Sons 🌐 German ⚖ 642 KB

## Abstract The reaction of photogenerated singlet oxygen with α‐ and β‐pinenes has been carefully re‐examined. α‐Pinene almost exclusively (99.3% yield) furnishes __trans__‐3‐hydroperoxy‐pin2(10)‐ene. However, detectable amounts of the three other possible products are also found, viz., __cis__‐3‐

Singlet and triplet photocycloaddition r
Singlet and triplet photocycloaddition reactions of 2-pyridones with propenoate and 2,4-pentadienotes, and the frontier molecular orbital analysis
✍ Takaaki Suishu; Seiichiro Tsuru; Tetsuro Shimo; Kenichi Somekawa 📂 Article 📅 1997 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 480 KB

## Abstract Regioselective photocycloadditions of 2‐pyridones (1) with 2,4‐pentadienoates (3) were analysed and compared with the reactions with propenoate (2), and origins of the different regioselectivities were inferred from frontier molecular orbital properties by the use of PM3‐CI method. Dir