[
    {
        "id": "authors:ymea5-ssk50",
        "collection": "authors",
        "collection_id": "ymea5-ssk50",
        "cite_using_url": "https://resolver.caltech.edu/CaltechAUTHORS:20151015-104931160",
        "type": "article",
        "title": "Evidence for Cyclohexyne and Cyclopentyne as Intermediates in the Coupling Reactions of Phenyllithium with 1-Chlorocyclohexene and 1-Chlorocyclopentene",
        "author": [
            {
                "family_name": "Montgomery",
                "given_name": "Lawrence K.",
                "clpid": "Montgomery-L-K"
            },
            {
                "family_name": "Scardiglia",
                "given_name": "F.",
                "clpid": "Scardiglia-F"
            },
            {
                "family_name": "Roberts",
                "given_name": "John D.",
                "clpid": "Roberts-J-D"
            }
        ],
        "abstract": "Phenyllithium and 1-chlorocyclohexene and 1-chlorocyclopentene react at 150\u00ba in ether to form 1-phenylcyclohexene and 1-phenylcyclopentene, respectively. A 1:1 mixture of 1-chlorocyclohexene-2-^(14) and 1-chlorocyclohexene-6 ^(14)- with phenyllithium yielded 1-phenylcyclohexene-x-^(14)C which contained 23 % of the ^(14)C label in the 1-position. When 1-chlorocyclopentene-1-^(14)C was heated with phenyllithium, extensive rearrangement of the ^(14)C label occurred with 48.9, 36.2, and 14.9% of the ^(14)C distributed in the 1-,2-, and 5-positions of 1-phenylcyclopentene, respectively. The observed ^(14)C rearrangements which accompanied these nucleophilic substitution reactions are best rationalized in terms of an elimination-addition mechanism involving cycloalkyne intermediates.",
        "doi": "10.1021/ja01087a015",
        "issn": "0002-7863",
        "publisher": "American Chemical Society",
        "publication": "Journal of the American Chemical Society",
        "publication_date": "1965-05-01",
        "series_number": "9",
        "volume": "87",
        "issue": "9",
        "pages": "1917-1925"
    }
]