𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Light-Induced Cycloaddition of 2,3-Dihydro-2,2-dimethyl-4H-thiopyran-4-one (a 4-Thiacyclohex-2-enone) to Alkenes and Dienes

✍ Scribed by Kerstin Schmidt; Jürgen Kopf; Paul Margaretha

Publisher
John Wiley and Sons
Year
2005
Tongue
German
Weight
213 KB
Volume
88
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The reactivity of (thiacyclic)‐2,3‐dihydro‐2,2‐dimethyl‐4__H__‐thiopyran‐4‐one (1a) in light‐induced cycloadditions to furan (F), acrylonitrile (AN), or 2,3‐dimethylbut‐2‐ene (TME) is compared to that of (carbocyclic) 5,5‐dimethylcyclohex‐2‐enone (1b). Whereas for the more‐flexible thiacycle, the efficiency of [2+2]‐photocycloadduct formation with AN or TME is generally much lower, the diastereoselectivity regarding the ring fusion in the bicyclo[4.2.0]octanes is quite similar for both enones. In contrast, 1a affords exclusively trans‐fused [4+2] cycloadducts with F, while 1b gives predominantly the corresponding cis‐fused products.

📜 SIMILAR VOLUMES

Light-Induced Cycloaddition of Furan and
Light-Induced Cycloaddition of Furan and addition of methanol to a 4-thiacyclohex-2-enone ( = 2,3-dihydro-4H-thiin-4-one) and a 4-thiacyclopent-2-enone ( = thiophen-3(2H)-one)
✍ Ronald Kowalewski; Paul Margaretha 📂 Article 📅 1992 🏛 John Wiley and Sons 🌐 German ⚖ 333 KB 👁 1 views

## Abstract Irradiation of newly synthesized 2,2‐dimethyl‐2,3‐dihydro‐4__H__‐thiin‐4‐one (1) in furan affords the two [4 + 2] cycloadducts 3 and 4 and the [2 + 2] cycloadduct 5 in a 5:4:1 ratio (__Scheme 1__). Irradiation of 1 in MeOH gives a 3:2 mixture of 5‐ and 6‐methoxy‐2,2‐dimethylthian‐4‐ones

ChemInform Abstract: Synthesis and Antim
ChemInform Abstract: Synthesis and Antimicrobial Screening of 5-(4,7-Dimethyl-2-oxo-2H-benzopyran-6-ylazo) -2-methyl-6-morpholin-4-yl-2,3-dihydro-3H-pyrimidin-4-one and 5-(4,7-Dimethyl-2-oxo-2H-benzopyran-6-ylazo) -2-methyl-6-piperidin-1-yl-2,3-dihydro-3H-pyrimidin-4-one.
✍ Vinata V. Mulwad; Sagar A. Mayekar 📂 Article 📅 2008 🏛 John Wiley and Sons ⚖ 36 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 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