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Addition Reactions of Sulfenyl and Sulfinyl Chlorides with 3-Phenyl-1-azabicyclo[1.1.0]butane

✍ Scribed by Grzegorz Mlostoń; Marta Woźnicka; Józef Drabowicz; Anthony Linden; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
2008
Tongue
German
Weight
250 KB
Volume
91
Category
Article
ISSN
0018-019X

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✦ Synopsis

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 intermediate carbenium ion, which is formed by the addition of the electrophile at the N‐atom and cleavage of the N(1)C(3) bond. The structures of 9b and 10b are established by X‐ray crystallography.

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Oligomer formation via reactions of 3-ethyl-1-azabicyclo[1.1.0]butane with arenesulfonyl azides
✍ Alan P. Marchand; Sulejman Alihodžić 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 707 KB

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.