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Ring-opening reactions of 3-substituted 1-azabicyclo[1.1.0]butane with dichlorocarbene

✍ Scribed by Grzegorz Mlostoń; Alberto Galindo; Romuald Bartnik; Alan R. Marchand; D. Rajagopal

Book ID
112131431
Publisher
Journal of Heterocyclic Chemistry
Year
1996
Tongue
English
Weight
345 KB
Volume
33
Category
Article
ISSN
0022-152X

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## Abstract Sterically congested 1‐azabicyclo[1.1.0]butanes **1** add hydrazoic acid smoothly at 0–5°, giving 3‐azidoazetidines **2** in good to excellent yields. After hydrogenolysis over Pd/C catalyst, compounds **2** were converted into __N__‐unsubstituted azetidin‐3‐amines **4**. Attempted redu

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Electrophilic additions of arenesulfonyl azides (i.e., TsN3 and NsN3) to 3-ethyl-1-azabicycio-[1.1.0]butane (1) in CDCI3 at 80"C has been observed to result in the formation of oligomeric products. The mechanism of these reactions probably involves the formation of a carbocationic intermediate, i.e.

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## Abstract The reactions of 3‐phenyl‐1‐azabicyclo[1.1.0]butane with __α__‐chlorosulfenyl chlorides and sulfinyl chlorides lead to the corresponding sulfenamides and sulfinamides, respectively, which possess an azetidine ring. It is proposed that a two‐step mechanism occurs involving an intermediat