DOI: 10.1246/bcsj.52.1488. New Ring Opening Reactions of Oxiranes with Aryl Carboxylates

New Ring Opening Reactions of Oxiranes with Aryl Carboxylates

10.1246/bcsj.52.1488

Crossref journal-article

Oxford University Press (OUP)

Bulletin of the Chemical Society of Japan (286)

Abstract

Abstract Oxiranes reacted with aryl esters in the presence of base. The reactions of aryl carboxylates with alkyloxiranes afforded almost exclusively 1-alkyl-2-(aryloxy) ethyl carboxylates, whereas the reactions with aryloxiranes gave a mixture of 1-aryl-2-(aryloxy) ethyl carboxylates and 2-aryl-2-(aryloxy) ethyl carboxylates. Similar results were also obtained in the reaction with S-aryl thiocarboxylates and diaryl carbonates. The rate of reaction between phenyl acetate and phenoxymethyloxirane (PMO) in the presence of tributylamine (n-Bu3N) as a catalyst has been determined in the temperature range 110 to 130 °C and may be expressed by –d[PMO]⁄dt=k2[n-Bu3N]·[PMO]. The apparent activation energy calculated from the Arrhenius plots is 85.8 kj/mol. The reaction catalyzed by tributylamine is assumed to proceed through zwitter ions, n-Bu3\overset+NCH2CH(R)O− and n-Bu3\overset+NCH(R)CH2O−, which attack aryl carboxylate.

Bibliography

Funahashi, K. (1979). New Ring Opening Reactions of Oxiranes with Aryl Carboxylates. Bulletin of the Chemical Society of Japan, 52(5), 1488â1492.

Authors 1

Kazutoshi Funahashi (first)

References 9 Referenced 27

{'key': '2024011714503036400_r1'}
{'key': '2024011714503036400_r2'}
10.1021/ja01191a018
10.1021/ja01178a059
{'key': '2024011714503036400_r5'}
{'key': '2024011714503036400_r6'}
10.1021/ac60129a035
10.1021/ja01170a036
10.1021/jo01083a020

Dates

Type	When
Created	19 years, 1 month ago (July 19, 2006, 11:14 p.m.)
Deposited	1 year, 7 months ago (Jan. 17, 2024, 9:51 a.m.)
Indexed	1 month, 3 weeks ago (July 6, 2025, 1:26 p.m.)
Issued	46 years, 4 months ago (May 1, 1979)
Published	46 years, 4 months ago (May 1, 1979)
Published Online	19 years, 4 months ago (April 19, 2006)
Published Print	46 years, 4 months ago (May 1, 1979)

Funders 0

None

BibTeX

@article{Funahashi_1979, title={New Ring Opening Reactions of Oxiranes with Aryl Carboxylates}, volume={52}, ISSN={1348-0634}, url={http://dx.doi.org/10.1246/bcsj.52.1488}, DOI={10.1246/bcsj.52.1488}, number={5}, journal={Bulletin of the Chemical Society of Japan}, publisher={Oxford University Press (OUP)}, author={Funahashi, Kazutoshi}, year={1979}, month=may, pages={1488–1492} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2025,
        7,
        6
      ]
    ],
    "date-time": "2025-07-06T17:26:41Z",
    "timestamp": 1751822801598
  },
  "reference-count": 9,
  "publisher": "Oxford University Press (OUP)",
  "issue": "5",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            1979,
            5,
            1
          ]
        ],
        "date-time": "1979-05-01T00:00:00Z",
        "timestamp": 294364800000
      },
      "content-version": "vor",
      "delay-in-days": 0,
      "URL": "https://academic.oup.com/pages/standard-publication-reuse-rights"
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        1979,
        5,
        1
      ]
    ]
  },
  "abstract": "<jats:title>Abstract</jats:title>\n               <jats:p>Oxiranes reacted with aryl esters in the presence of base. The reactions of aryl carboxylates with alkyloxiranes afforded almost exclusively 1-alkyl-2-(aryloxy) ethyl carboxylates, whereas the reactions with aryloxiranes gave a mixture of 1-aryl-2-(aryloxy) ethyl carboxylates and 2-aryl-2-(aryloxy) ethyl carboxylates. Similar results were also obtained in the reaction with S-aryl thiocarboxylates and diaryl carbonates. The rate of reaction between phenyl acetate and phenoxymethyloxirane (PMO) in the presence of tributylamine (n-Bu3N) as a catalyst has been determined in the temperature range 110 to 130 \u00b0C and may be expressed by \u2013d[PMO]\u2044dt=k2[n-Bu3N]\u00b7[PMO]. The apparent activation energy calculated from the Arrhenius plots is 85.8 kj/mol. The reaction catalyzed by tributylamine is assumed to proceed through zwitter ions, n-Bu3\\overset+NCH2CH(R)O\u2212 and n-Bu3\\overset+NCH(R)CH2O\u2212, which attack aryl carboxylate.</jats:p>",
  "DOI": "10.1246/bcsj.52.1488",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2006,
        7,
        20
      ]
    ],
    "date-time": "2006-07-20T03:14:46Z",
    "timestamp": 1153365286000
  },
  "page": "1488-1492",
  "source": "Crossref",
  "is-referenced-by-count": 27,
  "title": "New Ring Opening Reactions of Oxiranes with Aryl Carboxylates",
  "prefix": "10.1093",
  "volume": "52",
  "author": [
    {
      "given": "Kazutoshi",
      "family": "Funahashi",
      "sequence": "first",
      "affiliation": [
        {
          "name": "Central Research Institute, Teijin Ltd"
        }
      ]
    }
  ],
  "member": "286",
  "published-online": {
    "date-parts": [
      [
        2006,
        4,
        19
      ]
    ]
  },
  "reference": [
    {
      "key": "2024011714503036400_r1"
    },
    {
      "key": "2024011714503036400_r2"
    },
    {
      "key": "2024011714503036400_r3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja01191a018"
    },
    {
      "key": "2024011714503036400_r4",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja01178a059"
    },
    {
      "key": "2024011714503036400_r5"
    },
    {
      "key": "2024011714503036400_r6"
    },
    {
      "key": "2024011714503036400_r7",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ac60129a035"
    },
    {
      "key": "2024011714503036400_r8",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja01170a036"
    },
    {
      "key": "2024011714503036400_r9",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo01083a020"
    }
  ],
  "container-title": "Bulletin of the Chemical Society of Japan",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://academic.oup.com/bcsj/article-pdf/52/5/1488/56109907/bcsj.52.1488.pdf",
      "content-type": "application/pdf",
      "content-version": "vor",
      "intended-application": "syndication"
    },
    {
      "URL": "https://academic.oup.com/bcsj/article-pdf/52/5/1488/56109907/bcsj.52.1488.pdf",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2024,
        1,
        17
      ]
    ],
    "date-time": "2024-01-17T14:51:47Z",
    "timestamp": 1705503107000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://academic.oup.com/bcsj/article/52/5/1488/7357895"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        1979,
        5,
        1
      ]
    ]
  },
  "references-count": 9,
  "journal-issue": {
    "issue": "5",
    "published-online": {
      "date-parts": [
        [
          2006,
          4,
          19
        ]
      ]
    },
    "published-print": {
      "date-parts": [
        [
          1979,
          5,
          1
        ]
      ]
    }
  },
  "URL": "http://dx.doi.org/10.1246/bcsj.52.1488",
  "relation": {},
  "ISSN": [
    "0009-2673",
    "1348-0634"
  ],
  "subject": [],
  "published-other": {
    "date-parts": [
      [
        1979,
        5
      ]
    ]
  },
  "published": {
    "date-parts": [
      [
        1979,
        5,
        1
      ]
    ]
  }
}