𝔖 Bobbio Scriptorium
✦   LIBER   ✦

The chemistry of the highly reactive 2,6-bis(bromomethyl)-4-pyrone

✍ Scribed by Werner Löwe; Stefanie A. Brätter; Manuela Weber; Peter Luger; Joachim Buddrus

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
66 KB
Volume
38
Category
Article
ISSN
0022-152X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Under basic conditions 2,6‐bis(bromomethyl)‐4‐pyrone 8 reacts with tetraethylene glycol to yield the unexpected macrocycle 9, which is related to the antibiotic Kjellmanianone 10. We propose that this ring transformation proceeds via the cyclopropyl intermediate d (Scheme 2), which undergoes a ring opening reaction comparable to the Favorskii rearrangement. Also, 8 reacts with methanol/sodium methoxide to yield the 3(2__H__)‐furanone derivative 11, the formation of which is suggested to proceed via the intermediate k with a carbenium‐oxonium‐ion subunit (Scheme 3). The structure of the 3(2__H__)‐furanone derivative was confirmed by X‐ray analysis.

📜 SIMILAR VOLUMES

ChemInform Abstract: The Chemistry of th
ChemInform Abstract: The Chemistry of the Highly Reactive 2,6-Bis(bromomethyl)-4-pyrone.
✍ Werner Loewe; Stefanie A. Braetter; Manuela Weber; Peter Luger; Joachim Buddrus 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 31 KB

## 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

The solvates of 1,2-bis(bromomethyl)-3,4
The solvates of 1,2-bis(bromomethyl)-3,4,5,6-tetraphenylbenzene
✍ Paweł Szlachcic; Wojciech Migda; Katarzyna Stadnicka 📂 Article 📅 2007 🏛 Elsevier Science 🌐 English ⚖ 1013 KB

Solvates of 1,2-bis(bromomethyl)-3,4,5,6-tetraphenylbenzene (1) were obtained, and their crystal structures were determined by X-ray diffraction. Crystal structure analysis indicated the following chemical compositions of solvates: 1AEbenzene (2), 1AE1/2 toluene (3), 1AE1/2 chlorobenzene (4) and 1AE

The photodimerization of 2,3-dihydro-2,6
The photodimerization of 2,3-dihydro-2,6-dimethyl-4-pyrone
✍ Peter Yates; Donald J. MacGregor 📂 Article 📅 1969 🏛 Elsevier Science 🌐 French ⚖ 209 KB

The photodimerization of a,R-unsaturated ketones to give cyclobutanes has long been known (l), but the structural details of such photodimers have been