DOI: 10.1246/bcsj.43.1443. Umwandlung von Aldehyden in 2-monosubstituierte Aziridine. Reduktion von α-Chlor, Brom- und Sulfonyloxynitilen mit Lithiumaluminiumhydrid

Umwandlung von Aldehyden in 2-monosubstituierte Aziridine. Reduktion von α-Chlor, Brom- und Sulfonyloxynitilen mit Lithiumaluminiumhydrid

10.1246/bcsj.43.1443

Crossref journal-article

Oxford University Press (OUP)

Bulletin of the Chemical Society of Japan (286)

Abstract

Abstract The reductive cyclization of α-chloro, bromo- and sulfonyloxycarbonitriles are described. α-Chlorocarbonitriles were reduced by lithium aluminum hydride to afford aziridines in sufficient yields. The Walden inversion was found to take place in the cource of the reductive cyclization of S-α-chloroisocapronitrile. We have found the two-step conversion of aldehydes to 2-mono-substituted aziridines which consists of treating aldehydes with benzenesulfonyl chloride and alkali cyanide to form α-benzenesulfonyloxycarbonitriles which are reduced by lithium aluminum hydride to the corresponding aziridines. The reduction of α-bromocarbonitriles with the hydride yielded prim. amines together with the aziridines.

Bibliography

Ichimura, K., & Ohta, M. (1970). Umwandlung von Aldehyden in 2-monosubstituierte Aziridine. Reduktion von Î±-Chlor, Brom- und Sulfonyloxynitilen mit Lithiumaluminiumhydrid. Bulletin of the Chemical Society of Japan, 43(5), 1443â1450.

Authors 2

Kunihiro Ichimura (first)
Masaki Ohta (additional)

References 35 Referenced 14

{'key': '2024011911473086900_r1'}
10.1021/jo01278a006
10.1021/ja01508a024
10.1021/jo01349a036
10.1021/jo01277a019
{'key': '2024011911473086900_r6'}
{'key': '2024011911473086900_r7'}
{'key': '2024011911473086900_r8'}
{'key': '2024011911473086900_r9'}
{'key': '2024011911473086900_r10'}
{'key': '2024011911473086900_r11'}
{'key': '2024011911473086900_r12'}
{'key': '2024011911473086900_r13'}
{'key': '2024011911473086900_r14'}
{'key': '2024011911473086900_r15'}
{'key': '2024011911473086900_r16'}
10.1021/ja01503a045
10.1002/cber.19140470219
10.1021/jo01086a021
{'key': '2024011911473086900_r20'}
10.1002/hlca.19610440508
10.1021/jo01057a037
10.1021/ja01097a010
{'key': '2024011911473086900_r24'}
10.1021/ja01060a024
{'key': '2024011911473086900_r26'}
{'key': '2024011911473086900_r27'}
{'key': '2024011911473086900_r28'}
{'key': '2024011911473086900_r29'}
{'key': '2024011911473086900_r30'}
{'key': '2024011911473086900_r31'}
10.1021/ja01154a005
10.1021/jo01066a024
{'key': '2024011911473086900_r34'}
10.1021/ja01145a038

Dates

Type	When
Created	19 years, 1 month ago (July 19, 2006, 9:27 p.m.)
Deposited	1 year, 7 months ago (Jan. 19, 2024, 6:47 a.m.)
Indexed	1 year, 7 months ago (Jan. 19, 2024, 7:04 p.m.)
Issued	55 years, 3 months ago (May 1, 1970)
Published	55 years, 3 months ago (May 1, 1970)
Published Online	19 years, 4 months ago (March 27, 2006)
Published Print	55 years, 3 months ago (May 1, 1970)

Funders 0

None

BibTeX

@article{Ichimura_1970, title={Umwandlung von Aldehyden in 2-monosubstituierte Aziridine. Reduktion von α-Chlor, Brom- und Sulfonyloxynitilen mit Lithiumaluminiumhydrid}, volume={43}, ISSN={1348-0634}, url={http://dx.doi.org/10.1246/bcsj.43.1443}, DOI={10.1246/bcsj.43.1443}, number={5}, journal={Bulletin of the Chemical Society of Japan}, publisher={Oxford University Press (OUP)}, author={Ichimura, Kunihiro and Ohta, Masaki}, year={1970}, month=may, pages={1443–1450} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2024,
        1,
        20
      ]
    ],
    "date-time": "2024-01-20T00:04:18Z",
    "timestamp": 1705709058778
  },
  "reference-count": 35,
  "publisher": "Oxford University Press (OUP)",
  "issue": "5",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            1970,
            5,
            1
          ]
        ],
        "date-time": "1970-05-01T00:00:00Z",
        "timestamp": 10368000000
      },
      "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": [
      [
        1970,
        5,
        1
      ]
    ]
  },
  "abstract": "<jats:title>Abstract</jats:title>\n               <jats:p>The reductive cyclization of \u03b1-chloro, bromo- and sulfonyloxycarbonitriles are described. \u03b1-Chlorocarbonitriles were reduced by lithium aluminum hydride to afford aziridines in sufficient yields. The Walden inversion was found to take place in the cource of the reductive cyclization of S-\u03b1-chloroisocapronitrile. We have found the two-step conversion of aldehydes to 2-mono-substituted aziridines which consists of treating aldehydes with benzenesulfonyl chloride and alkali cyanide to form \u03b1-benzenesulfonyloxycarbonitriles which are reduced by lithium aluminum hydride to the corresponding aziridines. The reduction of \u03b1-bromocarbonitriles with the hydride yielded prim. amines together with the aziridines.</jats:p>",
  "DOI": "10.1246/bcsj.43.1443",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2006,
        7,
        20
      ]
    ],
    "date-time": "2006-07-20T01:27:46Z",
    "timestamp": 1153358866000
  },
  "page": "1443-1450",
  "source": "Crossref",
  "is-referenced-by-count": 14,
  "title": "Umwandlung von Aldehyden in 2-monosubstituierte Aziridine. Reduktion von \u03b1-Chlor, Brom- und Sulfonyloxynitilen mit Lithiumaluminiumhydrid",
  "prefix": "10.1093",
  "volume": "43",
  "author": [
    {
      "given": "Kunihiro",
      "family": "Ichimura",
      "sequence": "first",
      "affiliation": [
        {
          "name": "Laboratorium f\u00fcr Organische Chemie, Tokio Institut f\u00fcr Technologies, Tokio"
        }
      ]
    },
    {
      "given": "Masaki",
      "family": "Ohta",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Laboratorium f\u00fcr Organische Chemie, Tokio Institut f\u00fcr Technologies, Tokio"
        }
      ]
    }
  ],
  "member": "286",
  "published-online": {
    "date-parts": [
      [
        2006,
        3,
        27
      ]
    ]
  },
  "reference": [
    {
      "key": "2024011911473086900_r1"
    },
    {
      "key": "2024011911473086900_r2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo01278a006"
    },
    {
      "key": "2024011911473086900_r3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja01508a024"
    },
    {
      "key": "2024011911473086900_r4",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo01349a036"
    },
    {
      "key": "2024011911473086900_r5",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo01277a019"
    },
    {
      "key": "2024011911473086900_r6"
    },
    {
      "key": "2024011911473086900_r7"
    },
    {
      "key": "2024011911473086900_r8"
    },
    {
      "key": "2024011911473086900_r9"
    },
    {
      "key": "2024011911473086900_r10"
    },
    {
      "key": "2024011911473086900_r11"
    },
    {
      "key": "2024011911473086900_r12"
    },
    {
      "key": "2024011911473086900_r13"
    },
    {
      "key": "2024011911473086900_r14"
    },
    {
      "key": "2024011911473086900_r15"
    },
    {
      "key": "2024011911473086900_r16"
    },
    {
      "key": "2024011911473086900_r17",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja01503a045"
    },
    {
      "key": "2024011911473086900_r18",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/cber.19140470219"
    },
    {
      "key": "2024011911473086900_r19",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo01086a021"
    },
    {
      "key": "2024011911473086900_r20"
    },
    {
      "key": "2024011911473086900_r21",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/hlca.19610440508"
    },
    {
      "key": "2024011911473086900_r22",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo01057a037"
    },
    {
      "key": "2024011911473086900_r23",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja01097a010"
    },
    {
      "key": "2024011911473086900_r24"
    },
    {
      "key": "2024011911473086900_r25",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja01060a024"
    },
    {
      "key": "2024011911473086900_r26"
    },
    {
      "key": "2024011911473086900_r27"
    },
    {
      "key": "2024011911473086900_r28"
    },
    {
      "key": "2024011911473086900_r29"
    },
    {
      "key": "2024011911473086900_r30"
    },
    {
      "key": "2024011911473086900_r31"
    },
    {
      "key": "2024011911473086900_r32",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja01154a005"
    },
    {
      "key": "2024011911473086900_r33",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo01066a024"
    },
    {
      "key": "2024011911473086900_r34"
    },
    {
      "key": "2024011911473086900_r35",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja01145a038"
    }
  ],
  "container-title": "Bulletin of the Chemical Society of Japan",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://academic.oup.com/bcsj/article-pdf/43/5/1443/55952356/bcsj.43.1443.pdf",
      "content-type": "application/pdf",
      "content-version": "vor",
      "intended-application": "syndication"
    },
    {
      "URL": "https://academic.oup.com/bcsj/article-pdf/43/5/1443/55952356/bcsj.43.1443.pdf",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2024,
        1,
        19
      ]
    ],
    "date-time": "2024-01-19T11:47:40Z",
    "timestamp": 1705664860000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://academic.oup.com/bcsj/article/43/5/1443/7375463"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        1970,
        5,
        1
      ]
    ]
  },
  "references-count": 35,
  "journal-issue": {
    "issue": "5",
    "published-online": {
      "date-parts": [
        [
          2006,
          3,
          27
        ]
      ]
    },
    "published-print": {
      "date-parts": [
        [
          1970,
          5,
          1
        ]
      ]
    }
  },
  "URL": "http://dx.doi.org/10.1246/bcsj.43.1443",
  "relation": {},
  "ISSN": [
    "0009-2673",
    "1348-0634"
  ],
  "subject": [],
  "published-other": {
    "date-parts": [
      [
        1970,
        5
      ]
    ]
  },
  "published": {
    "date-parts": [
      [
        1970,
        5,
        1
      ]
    ]
  }
}