Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
REACTION OF TRICYCLO[4.2.2.02,5]DECA-3,7-DIENE DERIVATIVES IN DMSO
Tadashi SasakiAkihiro Kondo
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1978 Volume 7 Issue 1 Pages 113-114

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Abstract

Reaction of tricyclo[4.2.2.02,5]deca-3,7-diene derivatives 1 or 2 with DMSO-conc.HCl gave transannular methylthiolactonization product 3 and 3-chloro-4-methylthiotricyclo[4.2.2.02,5]dec-7-ene derivatives 4. Reaction of 1 or 2 with HBF4 in DMSO resulted in the protonation of the cyclohexene double bond. These results have been interpreted as the result of the orbital interaction of electrophile′s LUMO and olefin′s HOMO.

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