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The chemistry of small ring compounds. Part 44. Solvolysis of cyclopropyl sulfides and ethers

✍ Scribed by R. Jorritsma; H. Steinberg; Th. J. de Boer

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
684 KB
Volume
100
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

1‐Chlorocyclopropyl methyl ether and the corresponding sulfide are methanolysed without any rupture of the three‐membered ring. The solvolysis of 1‐halocyclopropyl sulfides has been studied kinetically and takes place via an S~N~1 mechanism. Methyl substituents in the cyclopropyl ring promote ring opening. This, and the effect of variation of the leaving group (Cl, Br, SMe~2~^⊕^), can be rationalised in terms of relative stabilities of intermediary substituted cyclopropyl and alkyl cations.

📜 SIMILAR VOLUMES

The chemistry of small ring compounds. P
The chemistry of small ring compounds. Part 43. Synthesis of 1-substituted cyclopropyl sulfides
✍ R. Jorritsma; H. Steinberg; Th. J. de Boer 📂 Article 📅 2010 🏛 Elsevier Science 🌐 English ⚖ 874 KB

## Abstract 1‐Hydroxy‐ and 1‐halocyclopropyl sulfides can be conveniently prepared starting from cyclopropanone. Cyclopropyl sulfides with halogen or a dimethylsulfonium group in the α‐position can be transformed into 1‐substituted cyclopropyl sulfides with a variety of nucleophiles. This means tha

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## Abstract 1‐(Alkylthio)cyclopropyl azides ‐ readily accessible from the corresponding chlorides and bromides ‐ are smoothly decomposed at 70°C with nitrogen evolution. The main process is a ring enlargement to 2‐(alkylthio)azetines **2**, accompanied by cleavage to thiocyanate and alkene. Reactio

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The chemistry of small ring compounds. Part 46. Reduction of 1-halocyclopropyl sulfides by thiolates
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## Abstract The reaction of 1‐halocyclopropyl sulfides with sodium alkanethiolates in protic or aprotic solvents leads to high yields of cyclopropyl sulfides, in which halogen has been replaced by hydrogen. The complementary oxidized product is, in most cases, the thioketone or thioaldehyde derived