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: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 75, No. 1, 2008, pp.119-129
Published online, 28th September, 2007
DOI: 10.3987/COM-07-11191
1H NMR Sulfinyl Group Substituent Effects of Dithiinodiazine S-Oxides as a Key for Structure Assignment of Parent Dithiinodiazines

Andrzej Maslankiewicz,* Maria J. Maslankiewicz, Andrzej Zieba, and Krzysztof Marciniec

*Department of Organic Chemistry, The Medical University of Silesia, Jagielloñska 4, 41-200 Sosnowiec, Poland

Abstract

1,4-Dithiinodipyridine 1 was prepared by reduction of 4-chloro-3-chlorosulfonylopyridine (8) with HI / H3PO3 system. Sulfur-assisted thermal isomerization of 1 resulted in a mixture of 1 and 2. Treatment of dithiinodiazines 1, 2, 5, and 6 with a nitrating mixture led almost selectively to respective S-monooxides 1a, 2a, 5a, and 6a. Due to the significant values of sulfinyl group substituent effects, 1H NMR spectra of 1,4-dithiino-S-oxides 1a, 2a, 5a, and 6a permitted for structure assignment of parent dithiins 1, 2, 5, and 6 and confirmed regioselectivity of the reaction of dithiins 1, 2, 5, and 6 with nitrating mixture.