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The chemistry of small ring compounds. Part 43. Synthesis of 1-substituted cyclopropyl sulfides

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

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

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✦ Synopsis

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 that the usual difficulties encountered with nucleophilic substitution at three‐membered rings ‐ i.e. low rates and ring opening — are largely removed by the presence of an alkylthio group at the same ring carbon atom as the leaving group.

📜 SIMILAR VOLUMES

The chemistry of small ring compounds. P
The chemistry of small ring compounds. Part 44. Solvolysis of cyclopropyl sulfides and ethers
✍ R. Jorritsma; H. Steinberg; Th. J. de Boer 📂 Article 📅 2010 🏛 Elsevier Science 🌐 English ⚖ 684 KB

## 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 cyclopropy

The chemistry of small ring compounds. P
The chemistry of small ring compounds. Part 46. Reduction of 1-halocyclopropyl sulfides by thiolates
✍ R. Jorritsma; H. Steinberg; Th. J. de Boer 📂 Article 📅 2010 🏛 Elsevier Science 🌐 English ⚖ 888 KB

## 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sodium alkanethiolates in protic or aprotic solvents leads to high yields of cyclopropyl sulfides, in which halogen has been replaced by hydrogen.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

The chemistry of small ring compounds. P
The chemistry of small ring compounds. Part 45 Thermolysis and photolysis of l-(alkylthio)cyclopropyl azides
✍ R. Jorritsma; H. Steinberg; Th. J. de Boer 📂 Article 📅 2010 🏛 Elsevier Science 🌐 English ⚖ 580 KB

## 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