Zwitterionic Ring-Opened Oxyphosphonium Species from the Ph<inf>3</inf>P-I<inf>2</inf> Mediated Reactions of Benzo[ d]oxazol-2(3 H)-ones with Secondary Amines

Zwitterionic Ring-Opened Oxyphosphonium Species from the Ph<inf>3</inf>P-I<inf>2</inf> Mediated Reactions of Benzo[ d]oxazol-2(3 H)-ones with Secondary Amines

Copyright © 2020 American Chemical Society. Instead of the expected substituted 2-aminobenzo[d]oxazoles, relatively stable ring-opened oxyphosphonium betaines were isolated for the first time from the Ph3P-I2-mediated reactions of benzo[d]oxazol-2(3H)-ones with acyclic secondary amines. The structur...

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Main Authors: Mookda Pattarawarapan, Nittaya Wiriya, Saranphong Yimklan, Sirilak Wangngae, Wong Phakhodee
Format: Journal
Published: 2020
Subjects:
Chemistry
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http://cmuir.cmu.ac.th/jspui/handle/6653943832/70397
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Institution: Chiang Mai University
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spelling th-cmuir.6653943832-703972020-10-14T08:29:05Z Zwitterionic Ring-Opened Oxyphosphonium Species from the Ph<inf>3</inf>P-I<inf>2</inf> Mediated Reactions of Benzo[ d]oxazol-2(3 H)-ones with Secondary Amines Mookda Pattarawarapan Nittaya Wiriya Saranphong Yimklan Sirilak Wangngae Wong Phakhodee Chemistry Copyright © 2020 American Chemical Society. Instead of the expected substituted 2-aminobenzo[d]oxazoles, relatively stable ring-opened oxyphosphonium betaines were isolated for the first time from the Ph3P-I2-mediated reactions of benzo[d]oxazol-2(3H)-ones with acyclic secondary amines. The structure of one of these compounds was unambiguously confirmed by single-crystal X-ray analysis. Thermolysis of the betaines gave rise to 2-dialkylaminobenzoxazoles with concomitant loss of triphenylphosphine oxide, suggesting their possible role as intermediates in an alternative reaction path. 2020-10-14T08:29:05Z 2020-10-14T08:29:05Z 2020-05-01 Journal 15206904 00223263 2-s2.0-85084706494 10.1021/acs.joc.0c00211 https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85084706494&origin=inward http://cmuir.cmu.ac.th/jspui/handle/6653943832/70397
institution Chiang Mai University
building Chiang Mai University Library
continent Asia
country Thailand
Thailand
content_provider Chiang Mai University Library
collection CMU Intellectual Repository
topic Chemistry
spellingShingle Chemistry
Mookda Pattarawarapan
Nittaya Wiriya
Saranphong Yimklan
Sirilak Wangngae
Wong Phakhodee
Zwitterionic Ring-Opened Oxyphosphonium Species from the Ph<inf>3</inf>P-I<inf>2</inf> Mediated Reactions of Benzo[ d]oxazol-2(3 H)-ones with Secondary Amines
description Copyright © 2020 American Chemical Society. Instead of the expected substituted 2-aminobenzo[d]oxazoles, relatively stable ring-opened oxyphosphonium betaines were isolated for the first time from the Ph3P-I2-mediated reactions of benzo[d]oxazol-2(3H)-ones with acyclic secondary amines. The structure of one of these compounds was unambiguously confirmed by single-crystal X-ray analysis. Thermolysis of the betaines gave rise to 2-dialkylaminobenzoxazoles with concomitant loss of triphenylphosphine oxide, suggesting their possible role as intermediates in an alternative reaction path.
format Journal
author Mookda Pattarawarapan
Nittaya Wiriya
Saranphong Yimklan
Sirilak Wangngae
Wong Phakhodee
author_facet Mookda Pattarawarapan
Nittaya Wiriya
Saranphong Yimklan
Sirilak Wangngae
Wong Phakhodee
author_sort Mookda Pattarawarapan
title Zwitterionic Ring-Opened Oxyphosphonium Species from the Ph<inf>3</inf>P-I<inf>2</inf> Mediated Reactions of Benzo[ d]oxazol-2(3 H)-ones with Secondary Amines
title_short Zwitterionic Ring-Opened Oxyphosphonium Species from the Ph<inf>3</inf>P-I<inf>2</inf> Mediated Reactions of Benzo[ d]oxazol-2(3 H)-ones with Secondary Amines
title_full Zwitterionic Ring-Opened Oxyphosphonium Species from the Ph<inf>3</inf>P-I<inf>2</inf> Mediated Reactions of Benzo[ d]oxazol-2(3 H)-ones with Secondary Amines
title_fullStr Zwitterionic Ring-Opened Oxyphosphonium Species from the Ph<inf>3</inf>P-I<inf>2</inf> Mediated Reactions of Benzo[ d]oxazol-2(3 H)-ones with Secondary Amines
title_full_unstemmed Zwitterionic Ring-Opened Oxyphosphonium Species from the Ph<inf>3</inf>P-I<inf>2</inf> Mediated Reactions of Benzo[ d]oxazol-2(3 H)-ones with Secondary Amines
title_sort zwitterionic ring-opened oxyphosphonium species from the ph<inf>3</inf>p-i<inf>2</inf> mediated reactions of benzo[ d]oxazol-2(3 h)-ones with secondary amines
publishDate 2020
url https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85084706494&origin=inward
http://cmuir.cmu.ac.th/jspui/handle/6653943832/70397
_version_ 1681752895313149952

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