DOI: 10.1002/recl.19730921205. Some aspects of the solution photochemistry of 1,3‐cyclohexadiene, <i>(Z)</i>‐ and <i>(E)</i>‐1,3,5‐hexatriene

Some aspects of the solution photochemistry of 1,3‐cyclohexadiene, (Z)‐ and (E)‐1,3,5‐hexatriene

10.1002/recl.19730921205

Crossref journal-article

Wiley

Recueil des Travaux Chimiques des Pays-Bas (311)

Abstract

AbstractUV irradiation (λ = 265 nm) of 1,3‐cyclohexadiene yields (Z)‐1,3,5‐hexatriene with good efficiency (Φ = 0.41). UV irradiation also effects equilibration between (Z)‐ and (E)‐isomers, be it with rather low quantum yields (ΦZ→E = 0.034; ΦZ→E =0.016). The Z ⇄ E isomerization can be sensitized by triplet sensitizers, e.g. biacetyl. This reaction occurred also upon irradiation of solutions in bromoform with light of 436 nm (So → T absorption).A simple formula for the calculation of quantum yields from composition data is given.

Bibliography

Minnaard, N. G., & Havinga, E. (1973). Some aspects of the solution photochemistry of 1,3âcyclohexadiene, (Z)â and (E)â1,3,5âhexatriene. Recueil Des Travaux Chimiques Des Pays-Bas, 92(12), 1315â1320. Portico.

Authors 2

N. G. Minnaard (first)
E. Havinga (additional)

References 33 Referenced 42

N. G.Minnaard Thesis Leiden 1970.
10.1002/recl.19600790905
10.1021/ja00757a056
10.1002/9780470133347.ch5
10.1021/cr60262a005
10.1007/BFb0051136
{'key': 'e_1_2_1_4_5', 'volume-title': 'Technique of Org. Chem.', 'author': 'Turro N. J.', 'year': '1969'} / Technique of Org. Chem. by Turro N. J. (1969)
10.1021/ja00749a037
10.1021/ja00767a042
10.1063/1.1733798
10.1021/ja00964a042
10.1021/ac60157a025
10.1007/BF00514598
aJ.Cornelisse Thesis Leiden 1966.
10.1515/znb-1964-0401 / Z. Naturforsch. by Mauser H. (1964)
10.1002/bbpc.19630670908
10.1515/znb-1964-0105 / Z. Naturforsch by Schenck G. O. (1964)
10.1021/ja01077a033
W. Th. A. M.van der LugtandL. J.Oosterhoff Chem. Commun.1235(1968). (10.1039/c19680001235)
10.1021/ja00774a033
aP. J.Vroegop Thesis Leiden 1972.
10.1016/S0040-4020(01)83160-4
10.1007/BF00529345
10.1002/9780470171868.ch1
N. G.MinnaardandE.Havinga preceeding paper.
{'key': 'e_1_2_1_16_2', 'first-page': '21', 'volume': '80', 'author': 'de van der R. J.', 'year': '1961', 'journal-title': 'Rec. Trav. Chim.'} / Rec. Trav. Chim. by de van der R. J. (1961)
10.1002/hlca.19570400116
10.1021/jo01046a543
10.1021/ja01495a036
{'key': 'e_1_2_1_19_3', 'first-page': '49', 'volume': '41', 'author': 'Hwa J. C. H.', 'year': '1962', 'journal-title': 'Org. Synth.'} / Org. Synth. by Hwa J. C. H. (1962)
10.1021/ja01091a050
10.1002/recl.19540730507
10.1098/rspa.1956.0102

Dates

Type	When
Created	14 years, 11 months ago (Sept. 13, 2010, 11:57 p.m.)
Deposited	1 year, 9 months ago (Nov. 13, 2023, 12:56 p.m.)
Indexed	1 year, 1 month ago (July 9, 2024, 3:53 a.m.)
Issued	52 years, 8 months ago (Jan. 1, 1973)
Published	52 years, 8 months ago (Jan. 1, 1973)
Published Online	15 years ago (Sept. 2, 2010)
Published Print	52 years, 8 months ago (Jan. 1, 1973)

Funders 0

None

BibTeX

@article{Minnaard_1973, title={Some aspects of the solution photochemistry of 1,3‐cyclohexadiene, (Z)‐ and (E)‐1,3,5‐hexatriene}, volume={92}, ISSN={0165-0513}, url={http://dx.doi.org/10.1002/recl.19730921205}, DOI={10.1002/recl.19730921205}, number={12}, journal={Recueil des Travaux Chimiques des Pays-Bas}, publisher={Wiley}, author={Minnaard, N. G. and Havinga, E.}, year={1973}, month=jan, pages={1315–1320} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2024,
        7,
        9
      ]
    ],
    "date-time": "2024-07-09T07:53:12Z",
    "timestamp": 1720511592307
  },
  "reference-count": 33,
  "publisher": "Wiley",
  "issue": "12",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            2010,
            9,
            2
          ]
        ],
        "date-time": "2010-09-02T00:00:00Z",
        "timestamp": 1283385600000
      },
      "content-version": "vor",
      "delay-in-days": 13758,
      "URL": "http://onlinelibrary.wiley.com/termsAndConditions#vor"
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        1973,
        1
      ]
    ]
  },
  "abstract": "<jats:title>Abstract</jats:title><jats:p>UV irradiation (\u03bb = 265 nm) of 1,3\u2010cyclohexadiene yields (<jats:italic>Z</jats:italic>)\u20101,3,5\u2010hexatriene with good efficiency (\u03a6 = 0.41). UV irradiation also effects equilibration between (<jats:italic>Z</jats:italic>)\u2010 and (<jats:italic>E</jats:italic>)\u2010isomers, be it with rather low quantum yields (\u03a6<jats:sub>Z\u2192E</jats:sub> = 0.034; \u03a6<jats:sub>Z\u2192E</jats:sub> =0.016). The <jats:italic>Z</jats:italic> \u21c4 <jats:italic>E</jats:italic> isomerization can be sensitized by triplet sensitizers, <jats:italic>e.g.</jats:italic> biacetyl. This reaction occurred also upon irradiation of solutions in bromoform with light of 436 nm (S<jats:sub>o</jats:sub> \u2192 T absorption).</jats:p><jats:p>A simple formula for the calculation of quantum yields from composition data is given.</jats:p>",
  "DOI": "10.1002/recl.19730921205",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2010,
        9,
        14
      ]
    ],
    "date-time": "2010-09-14T03:57:18Z",
    "timestamp": 1284436638000
  },
  "page": "1315-1320",
  "source": "Crossref",
  "is-referenced-by-count": 42,
  "title": "Some aspects of the solution photochemistry of 1,3\u2010cyclohexadiene, <i>(Z)</i>\u2010 and <i>(E)</i>\u20101,3,5\u2010hexatriene",
  "prefix": "10.1002",
  "volume": "92",
  "author": [
    {
      "given": "N. G.",
      "family": "Minnaard",
      "sequence": "first",
      "affiliation": []
    },
    {
      "given": "E.",
      "family": "Havinga",
      "sequence": "additional",
      "affiliation": []
    }
  ],
  "member": "311",
  "published-online": {
    "date-parts": [
      [
        2010,
        9,
        2
      ]
    ]
  },
  "reference": [
    {
      "key": "e_1_2_1_1_2",
      "unstructured": "N. G.Minnaard Thesis Leiden 1970."
    },
    {
      "key": "e_1_2_1_2_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/recl.19600790905"
    },
    {
      "key": "e_1_2_1_3_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00757a056"
    },
    {
      "key": "e_1_2_1_4_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/9780470133347.ch5"
    },
    {
      "key": "e_1_2_1_4_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cr60262a005"
    },
    {
      "key": "e_1_2_1_4_4",
      "doi-asserted-by": "publisher",
      "DOI": "10.1007/BFb0051136"
    },
    {
      "key": "e_1_2_1_4_5",
      "volume-title": "Technique of Org. Chem.",
      "author": "Turro N. J.",
      "year": "1969"
    },
    {
      "key": "e_1_2_1_4_6",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00749a037"
    },
    {
      "key": "e_1_2_1_4_7",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00767a042"
    },
    {
      "key": "e_1_2_1_5_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1063/1.1733798"
    },
    {
      "key": "e_1_2_1_6_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00964a042"
    },
    {
      "key": "e_1_2_1_7_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ac60157a025"
    },
    {
      "key": "e_1_2_1_7_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1007/BF00514598"
    },
    {
      "key": "e_1_2_1_8_2",
      "unstructured": "aJ.Cornelisse Thesis Leiden 1966."
    },
    {
      "key": "e_1_2_1_8_3",
      "doi-asserted-by": "crossref",
      "first-page": "180",
      "DOI": "10.1515/znb-1964-0401",
      "volume": "19",
      "author": "Mauser H.",
      "year": "1964",
      "journal-title": "Z. Naturforsch."
    },
    {
      "key": "e_1_2_1_8_4",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/bbpc.19630670908"
    },
    {
      "key": "e_1_2_1_9_2",
      "doi-asserted-by": "crossref",
      "first-page": "18",
      "DOI": "10.1515/znb-1964-0105",
      "volume": "19",
      "author": "Schenck G. O.",
      "year": "1964",
      "journal-title": "Z. Naturforsch"
    },
    {
      "key": "e_1_2_1_10_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja01077a033"
    },
    {
      "key": "e_1_2_1_11_2",
      "doi-asserted-by": "crossref",
      "unstructured": "W. Th. A. M.van der LugtandL. J.Oosterhoff Chem. Commun.1235(1968).",
      "DOI": "10.1039/c19680001235"
    },
    {
      "key": "e_1_2_1_11_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00774a033"
    },
    {
      "key": "e_1_2_1_12_2",
      "unstructured": "aP. J.Vroegop Thesis Leiden 1972."
    },
    {
      "key": "e_1_2_1_12_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4020(01)83160-4"
    },
    {
      "key": "e_1_2_1_13_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1007/BF00529345"
    },
    {
      "key": "e_1_2_1_14_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/9780470171868.ch1"
    },
    {
      "key": "e_1_2_1_15_2",
      "unstructured": "N. G.MinnaardandE.Havinga preceeding paper."
    },
    {
      "key": "e_1_2_1_16_2",
      "first-page": "21",
      "volume": "80",
      "author": "de van der R. J.",
      "year": "1961",
      "journal-title": "Rec. Trav. Chim."
    },
    {
      "key": "e_1_2_1_17_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/hlca.19570400116"
    },
    {
      "key": "e_1_2_1_18_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo01046a543"
    },
    {
      "key": "e_1_2_1_19_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja01495a036"
    },
    {
      "key": "e_1_2_1_19_3",
      "first-page": "49",
      "volume": "41",
      "author": "Hwa J. C. H.",
      "year": "1962",
      "journal-title": "Org. Synth."
    },
    {
      "key": "e_1_2_1_20_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja01091a050"
    },
    {
      "key": "e_1_2_1_21_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/recl.19540730507"
    },
    {
      "key": "e_1_2_1_22_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1098/rspa.1956.0102"
    }
  ],
  "container-title": "Recueil des Travaux Chimiques des Pays-Bas",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Frecl.19730921205",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "text-mining"
    },
    {
      "URL": "https://onlinelibrary.wiley.com/doi/pdf/10.1002/recl.19730921205",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2023,
        11,
        13
      ]
    ],
    "date-time": "2023-11-13T17:56:47Z",
    "timestamp": 1699898207000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://onlinelibrary.wiley.com/doi/10.1002/recl.19730921205"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        1973,
        1
      ]
    ]
  },
  "references-count": 33,
  "journal-issue": {
    "issue": "12",
    "published-print": {
      "date-parts": [
        [
          1973,
          1
        ]
      ]
    }
  },
  "alternative-id": [
    "10.1002/recl.19730921205"
  ],
  "URL": "http://dx.doi.org/10.1002/recl.19730921205",
  "relation": {},
  "ISSN": [
    "0165-0513",
    "0165-0513"
  ],
  "subject": [],
  "container-title-short": "Recl. Trav. Chim. Pays\u2010Bas",
  "published": {
    "date-parts": [
      [
        1973,
        1
      ]
    ]
  }
}