Rearrangements of the Allyl Group in the Thermolysis of 1,8-Bis(allylthio)-and 1,8-Bis(allylseleno)naphthalene Monooxides via Through-space Interaction between Two Sulfur and Selenium Atoms

1,8-Bis(allylthio)- and 1,8-bis(allylseleno)naphthalene monooxides underwent facile mulliallylic rearrangements to give 2-allyl-substituted naphtho[1,8-cd]-1,2-dithioles and naphtho[1,8-cd]-1,2 diselenoles under mild conditions via the sulfur-sulfur and selenium-selenium through-space interaction. T...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 1995-11, Vol.51 (45), p.12239-12256
Main Authors: Shima, Hidetaka, Furukawa, Naomichi
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:1,8-Bis(allylthio)- and 1,8-bis(allylseleno)naphthalene monooxides underwent facile mulliallylic rearrangements to give 2-allyl-substituted naphtho[1,8-cd]-1,2-dithioles and naphtho[1,8-cd]-1,2 diselenoles under mild conditions via the sulfur-sulfur and selenium-selenium through-space interaction. The mechanism for the reaction has been determined by D-tracer and cross-over experiments.
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(95)00791-6