Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Report | Regular issue | Vol 16, No. 5, 1981, pp.789-792
Published online, 1st January, 1970
DOI: 10.3987/R-1981-05-0789
The Cycloaddition Reaction of 4,6-Diphenylthieno[3,4-c][1,2,5]oxadiazole with Norbornene

Otohiko Tsuge,* Toshiaki Takata, and Michihiko Noguchi

*Research Institute of Industrial Science, Faculty of Engineering, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan


4,6-Diphenylthieno[3,4-c][1,2,5]oxadiazole containing tetra-valent sulfur reacted with norbornene to give four stereoisomeric 1:2 adducts, isoxazolinyltetrahydrothiophene derivatives. The reaction proceeds via initial formation of both the endo-exo and exo-exo cycloadducts across the thiocarbonyl ylide dipole. Subsequent ring cleavage of the oxadiazole ring of initial strained cycloadducts generates the nitrile oxide intermediates capable of undergoing cycloaddition to norbornene to afford the 1:2 adducts.