Regioselective monohalogenation of 3,3-disubstituted bornane-2-thiones via thione–dihalogen complexes

Reaction of 3,3-disubstituted bornane-2-thiones with Br 2, ICl, or Cl 2 afforded the corresponding 10-bromobornane-2-thiones, 10-iodobornane-2-thiones, or the products originated from skeletal rearrangement of 10-chlorobornane-2-thiones, respectively. Reaction of 3,3-disubstituted bornane-2-thiones...

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Bibliographic Details
Published in:Tetrahedron letters 2001-08, Vol.42 (35), p.6167-6169
Main Authors: Shimada, Kazuaki, Nanae, Takashi, Aoyagi, Shigenobu, Takikawa, Yuji, Kabuto, Chizuko
Format: Article
Language:English
Subjects:
10-halobornane-2-thione
bornane-2-thione
dihalosulfurane
halogenation
thione–I 2 CT complex
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Summary:Reaction of 3,3-disubstituted bornane-2-thiones with Br 2, ICl, or Cl 2 afforded the corresponding 10-bromobornane-2-thiones, 10-iodobornane-2-thiones, or the products originated from skeletal rearrangement of 10-chlorobornane-2-thiones, respectively. Reaction of 3,3-disubstituted bornane-2-thiones A with 1 molar amount of Br 2 afforded 10-bromobornane-2-thiones C in almost quantitative yields. The regioselective bromination of A was assumed to proceed through intermediary dibromosulfuranes B .
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(01)01235-7