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X-ray crystallographic and NMR structural studies of trans-2,3-dichloro-5-ethyl-2,3-dihydrothieno[2 3-b]pyridine syn-1-oxide reactions of thiophene rings with hypochlorite reagents

✍ Scribed by Leroy H. Klemm; Timothy J. R. Weakley; Myungok Yoon

Publisher
Journal of Heterocyclic Chemistry
Year
1999
Tongue
English
Weight
252 KB
Volume
36
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

X‐ray analysis of a crystalline product obtained by treatment of 5‐ethylthieno[2,3‐b]pyridine with excess acidified hypochlorite establishes its stereochemistry as trans‐2,3‐dichloro‐5‐ethyl‐2,3‐dihydrothieno‐[2,3‐b]pyridine syn‐1‐oxide (5), wherein the pyridine ring is planar and the dihydrothiophene ring is non‐planar with a C2‐S‐C7a angle of 86.6°. The trans geometry is corroborated by a proton‐proton coupling constant J~2,3~ of 6.8 Hz. Comparison of ^1^H and ^13^C nmr data for 5 with analogous crystalline 2,3‐dichloro‐1‐oxide addenda isolated in the isosteric benzo[b]thiophene and thieno[2,3‐b]pyridine parent systems indicates that some proposed stereochemical assignments are questionable.

📜 SIMILAR VOLUMES

ChemInform Abstract: X-Ray Crystallograp
ChemInform Abstract: X-Ray Crystallographic and NMR Structural Studies of trans-2,3-Dichloro-5-ethyl-2,3-dihydrothieno[2,3-b]pyridine syn-1-Oxide. Reactions of Thiophene Rings with Hypochlorite Reagents.
✍ LeRoy H. Klemm; Timothy J. R. Weakley; Myungok Yoon 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 29 KB 👁 2 views

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