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Cycloaddition of N-(2,2,2-trichloroethylidene)-substituted carboxamides and carbamates to 1,2,4-thiadiazol-5(2H)-imines

✍ Scribed by Vladimir S. Zyabrev; Mikhail A. Rensky; Eduard B. Rusanov; Boris S. Drach

Book ID
102231791
Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
122 KB
Volume
14
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

1,2,4‐Thiadiazol‐5(2H)‐imines 4 react with N‐(2,2,2‐trichloroethylidene)‐substituted amides 5 to form [3 + 2]‐cycloaddition products 6 featured by an extra coordination of the ring sulfur atom to the terminal nitrogen atom of the side 1,3‐diazapropenylidene group, as established by X‐ray diffraction investigation. This coordination evidently plays an important role in the alkylation of compounds 6 into 8 at the oxygen atom under mild conditions. The SN bond “switch‐over” restoring the original 1,2,4‐thiadiazole ring occurs therewith. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:474–480, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10182

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✍ V. S. Zyabrev; M. A. Renskii; B. S. Drach 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 29 KB 👁 2 views

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