2-Thiabicyclo[3.2.0]hepta-3,6-Dienes. 3. Desulfuration and Sulfuration of 2-Thiabicyclo[3.2.0]hepta-3,6-Dienes and X-Ray Crystal Structure of 3a,6,7,8,9,9a-Hexahydro-3a,5-Dimethylthieno[3,2-B][2]benzothiophene-2,3-Dicarbonitrile

Richard H. Hall; Herman J. den Hertog; David N. Reinhoudt; Sybolt Harkema; Gerrit J. van Hummel; Jos W.H.M. Uiterwijk

doi:10.1021/jo00345a016

2-Thiabicyclo[3.2.0]hepta-3,6-Dienes. 3. Desulfuration and Sulfuration of 2-Thiabicyclo[3.2.0]hepta-3,6-Dienes and X-Ray Crystal Structure of 3a,6,7,8,9,9a-Hexahydro-3a,5-Dimethylthieno[3,2-B][2]benzothiophene-2,3-Dicarbonitrile

Richard H. Hall
, Herman J. den Hertog
, David N. Reinhoudt
, Sybolt Harkema
, Gerrit J. van Hummel
, Jos W.H.M. Uiterwijk

Missouri University of Science and Technonlogy

Research output: Contribution to journal › Article › peer-review

Abstract

The 2-3.2.0] hepta-3,6-Dienes 1–7 Extrude Sulfur in Solution at 285 °C to Give the 1,2-Benzenedicarbonitriles 8–12 in Yields of 42–56%. 5-(1,1-Dimethylethyl)-3,6-Dimethyl-2-3.2.0] hepta-3,6-Diene-1,7-Dicarbonitrile (6) Reacts at 140 °C to Give a Mixture of the Cope-Rearranged Isomer 13, the 1,2-Benzenedicarbonitrile 11, and possibly a 3a,6a-Dihydrothieno[3,2-B] thiophene (14). Reaction of 2a,5,6,7,8,8a-Hexahydro-2a,4-Dimethylbenzo[C]cyclobuta[B]thiophene-L,2-Dicarbonitrile (15) at 140 °C Gives a Mixture of De8ulfurated (16) and Sulfureted (17) Products in Yields of 88% and 70%, Respectively. Single-Crystal X-Ray Analysis Proved the 3a,6,7,8,9,9a-Hexahydrothieno[3,2-B][2]benzothiophene Structure (17). the Possible Mechanism of the Insertion of Sulfur in the Carbon-Carbon Single Bond of 15 is Discussed. © 1982, American Chemical Society. All Rights Reserved.

Original language	American English
Journal	Journal of Organic Chemistry
Volume	47
DOIs	https://doi.org/10.1021/jo00345a016
State	Published - Jan 1 1982
Externally published	Yes

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Hall, R. H., den Hertog, H. J., Reinhoudt, D. N., Harkema, S., van Hummel, G. J., & Uiterwijk, J. W. H. M. (1982). 2-Thiabicyclo[3.2.0]hepta-3,6-Dienes. 3. Desulfuration and Sulfuration of 2-Thiabicyclo[3.2.0]hepta-3,6-Dienes and X-Ray Crystal Structure of 3a,6,7,8,9,9a-Hexahydro-3a,5-Dimethylthieno[3,2-B][2]benzothiophene-2,3-Dicarbonitrile. Journal of Organic Chemistry, 47. https://doi.org/10.1021/jo00345a016

2-Thiabicyclo[3.2.0]hepta-3,6-Dienes. 3. Desulfuration and Sulfuration of 2-Thiabicyclo[3.2.0]hepta-3,6-Dienes and X-Ray Crystal Structure of 3a,6,7,8,9,9a-Hexahydro-3a,5-Dimethylthieno[3,2-B][2]benzothiophene-2,3-Dicarbonitrile. / Hall, Richard H.; den Hertog, Herman J.; Reinhoudt, David N. et al.
In: Journal of Organic Chemistry, Vol. 47, 01.01.1982.

Research output: Contribution to journal › Article › peer-review

Hall, RH, den Hertog, HJ, Reinhoudt, DN, Harkema, S, van Hummel, GJ & Uiterwijk, JWHM 1982, '2-Thiabicyclo[3.2.0]hepta-3,6-Dienes. 3. Desulfuration and Sulfuration of 2-Thiabicyclo[3.2.0]hepta-3,6-Dienes and X-Ray Crystal Structure of 3a,6,7,8,9,9a-Hexahydro-3a,5-Dimethylthieno[3,2-B][2]benzothiophene-2,3-Dicarbonitrile', Journal of Organic Chemistry, vol. 47. https://doi.org/10.1021/jo00345a016

Hall RH, den Hertog HJ, Reinhoudt DN, Harkema S, van Hummel GJ, Uiterwijk JWHM. 2-Thiabicyclo[3.2.0]hepta-3,6-Dienes. 3. Desulfuration and Sulfuration of 2-Thiabicyclo[3.2.0]hepta-3,6-Dienes and X-Ray Crystal Structure of 3a,6,7,8,9,9a-Hexahydro-3a,5-Dimethylthieno[3,2-B][2]benzothiophene-2,3-Dicarbonitrile. Journal of Organic Chemistry. 1982 Jan 1;47. doi: 10.1021/jo00345a016

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title = "2-Thiabicyclo[3.2.0]hepta-3,6-Dienes. 3. Desulfuration and Sulfuration of 2-Thiabicyclo[3.2.0]hepta-3,6-Dienes and X-Ray Crystal Structure of 3a,6,7,8,9,9a-Hexahydro-3a,5-Dimethylthieno[3,2-B][2]benzothiophene-2,3-Dicarbonitrile",

abstract = " The 2-3.2.0] hepta-3,6-Dienes 1{\textendash}7 Extrude Sulfur in Solution at 285 °C to Give the 1,2-Benzenedicarbonitriles 8{\textendash}12 in Yields of 42{\textendash}56\%. 5-(1,1-Dimethylethyl)-3,6-Dimethyl-2-3.2.0] hepta-3,6-Diene-1,7-Dicarbonitrile (6) Reacts at 140 °C to Give a Mixture of the Cope-Rearranged Isomer 13, the 1,2-Benzenedicarbonitrile 11, and possibly a 3a,6a-Dihydrothieno[3,2-B] thiophene (14). Reaction of 2a,5,6,7,8,8a-Hexahydro-2a,4-Dimethylbenzo[C]cyclobuta[B]thiophene-L,2-Dicarbonitrile (15) at 140 °C Gives a Mixture of De8ulfurated (16) and Sulfureted (17) Products in Yields of 88\% and 70\%, Respectively. Single-Crystal X-Ray Analysis Proved the 3a,6,7,8,9,9a-Hexahydrothieno[3,2-B][2]benzothiophene Structure (17). the Possible Mechanism of the Insertion of Sulfur in the Carbon-Carbon Single Bond of 15 is Discussed. {\textcopyright} 1982, American Chemical Society. All Rights Reserved.",

author = "Hall, \{Richard H.\} and \{den Hertog\}, \{Herman J.\} and Reinhoudt, \{David N.\} and Sybolt Harkema and \{van Hummel\}, \{Gerrit J.\} and Uiterwijk, \{Jos W.H.M.\}",

year = "1982",

month = jan,

day = "1",

doi = "10.1021/jo00345a016",

language = "American English",

volume = "47",

journal = "Journal of Organic Chemistry",

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T1 - 2-Thiabicyclo[3.2.0]hepta-3,6-Dienes. 3. Desulfuration and Sulfuration of 2-Thiabicyclo[3.2.0]hepta-3,6-Dienes and X-Ray Crystal Structure of 3a,6,7,8,9,9a-Hexahydro-3a,5-Dimethylthieno[3,2-B][2]benzothiophene-2,3-Dicarbonitrile

AU - Hall, Richard H.

AU - den Hertog, Herman J.

AU - Reinhoudt, David N.

AU - Harkema, Sybolt

AU - van Hummel, Gerrit J.

AU - Uiterwijk, Jos W.H.M.

PY - 1982/1/1

Y1 - 1982/1/1

N2 - The 2-3.2.0] hepta-3,6-Dienes 1–7 Extrude Sulfur in Solution at 285 °C to Give the 1,2-Benzenedicarbonitriles 8–12 in Yields of 42–56%. 5-(1,1-Dimethylethyl)-3,6-Dimethyl-2-3.2.0] hepta-3,6-Diene-1,7-Dicarbonitrile (6) Reacts at 140 °C to Give a Mixture of the Cope-Rearranged Isomer 13, the 1,2-Benzenedicarbonitrile 11, and possibly a 3a,6a-Dihydrothieno[3,2-B] thiophene (14). Reaction of 2a,5,6,7,8,8a-Hexahydro-2a,4-Dimethylbenzo[C]cyclobuta[B]thiophene-L,2-Dicarbonitrile (15) at 140 °C Gives a Mixture of De8ulfurated (16) and Sulfureted (17) Products in Yields of 88% and 70%, Respectively. Single-Crystal X-Ray Analysis Proved the 3a,6,7,8,9,9a-Hexahydrothieno[3,2-B][2]benzothiophene Structure (17). the Possible Mechanism of the Insertion of Sulfur in the Carbon-Carbon Single Bond of 15 is Discussed. © 1982, American Chemical Society. All Rights Reserved.

AB - The 2-3.2.0] hepta-3,6-Dienes 1–7 Extrude Sulfur in Solution at 285 °C to Give the 1,2-Benzenedicarbonitriles 8–12 in Yields of 42–56%. 5-(1,1-Dimethylethyl)-3,6-Dimethyl-2-3.2.0] hepta-3,6-Diene-1,7-Dicarbonitrile (6) Reacts at 140 °C to Give a Mixture of the Cope-Rearranged Isomer 13, the 1,2-Benzenedicarbonitrile 11, and possibly a 3a,6a-Dihydrothieno[3,2-B] thiophene (14). Reaction of 2a,5,6,7,8,8a-Hexahydro-2a,4-Dimethylbenzo[C]cyclobuta[B]thiophene-L,2-Dicarbonitrile (15) at 140 °C Gives a Mixture of De8ulfurated (16) and Sulfureted (17) Products in Yields of 88% and 70%, Respectively. Single-Crystal X-Ray Analysis Proved the 3a,6,7,8,9,9a-Hexahydrothieno[3,2-B][2]benzothiophene Structure (17). the Possible Mechanism of the Insertion of Sulfur in the Carbon-Carbon Single Bond of 15 is Discussed. © 1982, American Chemical Society. All Rights Reserved.

UR - https://scholarsmine.mst.edu/bio_inftec_facwork/504

U2 - 10.1021/jo00345a016

DO - 10.1021/jo00345a016

M3 - Article

SN - 1520-6904

VL - 47

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

ER -

2-Thiabicyclo[3.2.0]hepta-3,6-Dienes. 3. Desulfuration and Sulfuration of 2-Thiabicyclo[3.2.0]hepta-3,6-Dienes and X-Ray Crystal Structure of 3a,6,7,8,9,9a-Hexahydro-3a,5-Dimethylthieno[3,2-B][2]benzothiophene-2,3-Dicarbonitrile

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