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Benzocyclobutene— o -xylylene valence tautomerization: Oxygen and sulfur analogs

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Zeitschriftentitel: Proceedings of the National Academy of Sciences
Personen und Körperschaften: Mao, Yuh-Lin, Boekelheide, V.
In: Proceedings of the National Academy of Sciences, 77, 1980, 4, S. 1732-1735
Format: E-Article
Sprache: Englisch
veröffentlicht:
Proceedings of the National Academy of Sciences
Schlagwörter:
Multidisciplinary
author_facet Mao, Yuh-Lin
Boekelheide, V.
Mao, Yuh-Lin
Boekelheide, V.
author Mao, Yuh-Lin
Boekelheide, V.
spellingShingle Mao, Yuh-Lin
Boekelheide, V.
Proceedings of the National Academy of Sciences
Benzocyclobutene— o -xylylene valence tautomerization: Oxygen and sulfur analogs
Multidisciplinary
author_sort mao, yuh-lin
spelling Mao, Yuh-Lin Boekelheide, V. 0027-8424 1091-6490 Proceedings of the National Academy of Sciences Multidisciplinary http://dx.doi.org/10.1073/pnas.77.4.1732 <jats:p> Gas phase pyrolysis of <jats:italic>o</jats:italic> -hydroxybenzyl alcohol at 750°C gave <jats:italic>o</jats:italic> -quinonemethide, which, on isolation, formed a mixture of the corresponding dimer and trimer. However, pyrolysis of <jats:italic>o</jats:italic> -hydroxy-[1-(4-pentenyl)]benzyl alcohol permitted intramolecular trapping of the intermediate <jats:italic>o</jats:italic> -quinonemethide, giving 3,4-trimethylene-3,4-dihydrobenzochroman. In contrast, gas phase pyrolysis of <jats:italic>o</jats:italic> -mercaptobenzyl alcohol readily gave benzo[ <jats:italic>b</jats:italic> ]thiete in good yield. The pyrolysis makes this interesting highly strained molecule readily available for study and synthetic application. Preliminary results showed that benzo[ <jats:italic>b</jats:italic> ]thiete readily undergoes thermal dimerization, ring-opening reactions with nucleophiles, and a variety of Diels-Alder reactions. </jats:p> Benzocyclobutene— <i>o</i> -xylylene valence tautomerization: Oxygen and sulfur analogs Proceedings of the National Academy of Sciences
doi_str_mv 10.1073/pnas.77.4.1732
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series Proceedings of the National Academy of Sciences
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title Benzocyclobutene— o -xylylene valence tautomerization: Oxygen and sulfur analogs
title_unstemmed Benzocyclobutene— o -xylylene valence tautomerization: Oxygen and sulfur analogs
title_full Benzocyclobutene— o -xylylene valence tautomerization: Oxygen and sulfur analogs
title_fullStr Benzocyclobutene— o -xylylene valence tautomerization: Oxygen and sulfur analogs
title_full_unstemmed Benzocyclobutene— o -xylylene valence tautomerization: Oxygen and sulfur analogs
title_short Benzocyclobutene— o -xylylene valence tautomerization: Oxygen and sulfur analogs
title_sort benzocyclobutene— <i>o</i> -xylylene valence tautomerization: oxygen and sulfur analogs
topic Multidisciplinary
url http://dx.doi.org/10.1073/pnas.77.4.1732
publishDate 1980
physical 1732-1735
description <jats:p> Gas phase pyrolysis of <jats:italic>o</jats:italic> -hydroxybenzyl alcohol at 750°C gave <jats:italic>o</jats:italic> -quinonemethide, which, on isolation, formed a mixture of the corresponding dimer and trimer. However, pyrolysis of <jats:italic>o</jats:italic> -hydroxy-[1-(4-pentenyl)]benzyl alcohol permitted intramolecular trapping of the intermediate <jats:italic>o</jats:italic> -quinonemethide, giving 3,4-trimethylene-3,4-dihydrobenzochroman. In contrast, gas phase pyrolysis of <jats:italic>o</jats:italic> -mercaptobenzyl alcohol readily gave benzo[ <jats:italic>b</jats:italic> ]thiete in good yield. The pyrolysis makes this interesting highly strained molecule readily available for study and synthetic application. Preliminary results showed that benzo[ <jats:italic>b</jats:italic> ]thiete readily undergoes thermal dimerization, ring-opening reactions with nucleophiles, and a variety of Diels-Alder reactions. </jats:p>
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author Mao, Yuh-Lin, Boekelheide, V.
author_facet Mao, Yuh-Lin, Boekelheide, V., Mao, Yuh-Lin, Boekelheide, V.
author_sort mao, yuh-lin
container_issue 4
container_start_page 1732
container_title Proceedings of the National Academy of Sciences
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description <jats:p> Gas phase pyrolysis of <jats:italic>o</jats:italic> -hydroxybenzyl alcohol at 750°C gave <jats:italic>o</jats:italic> -quinonemethide, which, on isolation, formed a mixture of the corresponding dimer and trimer. However, pyrolysis of <jats:italic>o</jats:italic> -hydroxy-[1-(4-pentenyl)]benzyl alcohol permitted intramolecular trapping of the intermediate <jats:italic>o</jats:italic> -quinonemethide, giving 3,4-trimethylene-3,4-dihydrobenzochroman. In contrast, gas phase pyrolysis of <jats:italic>o</jats:italic> -mercaptobenzyl alcohol readily gave benzo[ <jats:italic>b</jats:italic> ]thiete in good yield. The pyrolysis makes this interesting highly strained molecule readily available for study and synthetic application. Preliminary results showed that benzo[ <jats:italic>b</jats:italic> ]thiete readily undergoes thermal dimerization, ring-opening reactions with nucleophiles, and a variety of Diels-Alder reactions. </jats:p>
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imprint Proceedings of the National Academy of Sciences, 1980
imprint_str_mv Proceedings of the National Academy of Sciences, 1980
institution DE-D275, DE-Bn3, DE-Brt1, DE-Zwi2, DE-D161, DE-Gla1, DE-Zi4, DE-15, DE-Pl11, DE-Rs1, DE-105, DE-14, DE-Ch1, DE-L229
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physical 1732-1735
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spelling Mao, Yuh-Lin Boekelheide, V. 0027-8424 1091-6490 Proceedings of the National Academy of Sciences Multidisciplinary http://dx.doi.org/10.1073/pnas.77.4.1732 <jats:p> Gas phase pyrolysis of <jats:italic>o</jats:italic> -hydroxybenzyl alcohol at 750°C gave <jats:italic>o</jats:italic> -quinonemethide, which, on isolation, formed a mixture of the corresponding dimer and trimer. However, pyrolysis of <jats:italic>o</jats:italic> -hydroxy-[1-(4-pentenyl)]benzyl alcohol permitted intramolecular trapping of the intermediate <jats:italic>o</jats:italic> -quinonemethide, giving 3,4-trimethylene-3,4-dihydrobenzochroman. In contrast, gas phase pyrolysis of <jats:italic>o</jats:italic> -mercaptobenzyl alcohol readily gave benzo[ <jats:italic>b</jats:italic> ]thiete in good yield. The pyrolysis makes this interesting highly strained molecule readily available for study and synthetic application. Preliminary results showed that benzo[ <jats:italic>b</jats:italic> ]thiete readily undergoes thermal dimerization, ring-opening reactions with nucleophiles, and a variety of Diels-Alder reactions. </jats:p> Benzocyclobutene— <i>o</i> -xylylene valence tautomerization: Oxygen and sulfur analogs Proceedings of the National Academy of Sciences
spellingShingle Mao, Yuh-Lin, Boekelheide, V., Proceedings of the National Academy of Sciences, Benzocyclobutene— o -xylylene valence tautomerization: Oxygen and sulfur analogs, Multidisciplinary
title Benzocyclobutene— o -xylylene valence tautomerization: Oxygen and sulfur analogs
title_full Benzocyclobutene— o -xylylene valence tautomerization: Oxygen and sulfur analogs
title_fullStr Benzocyclobutene— o -xylylene valence tautomerization: Oxygen and sulfur analogs
title_full_unstemmed Benzocyclobutene— o -xylylene valence tautomerization: Oxygen and sulfur analogs
title_short Benzocyclobutene— o -xylylene valence tautomerization: Oxygen and sulfur analogs
title_sort benzocyclobutene— <i>o</i> -xylylene valence tautomerization: oxygen and sulfur analogs
title_unstemmed Benzocyclobutene— o -xylylene valence tautomerization: Oxygen and sulfur analogs
topic Multidisciplinary
url http://dx.doi.org/10.1073/pnas.77.4.1732