Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
Shopping Cart: ( empty )
You are here: Home > Journals > CH > CH13449
RESEARCH ARTICLE
Contents Vol 67(3)

Reactions of Adamantanethione with Ketenes: Formation of a 1,3,5-Dioxathiane

Nicholas Drinnan A and Curt Wentrup A B
+ Author Affiliations
- Author Affiliations

A School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, Australia.

B Corresponding author. Email: wentrup@uq.edu.au

Australian Journal of Chemistry 67(3) 525-527 https://doi.org/10.1071/CH13449
Submitted: 28 August 2013  Accepted: 17 September 2013   Published: 1 October 2013

Abstract

The reaction between adamantanethione 1 and diphenylketene 9 yields 2,4-bis(diphenylmethylidene)-1,3,5-dioxathiane 14 via ketene–thione zwitterions. This is the first example of the formation of a 1,3,5-dioxathiane in a ketene reaction.


References

[1]  G. Mloston, H. Heimgartner, Curr. Org. Chem. 2011, 15, 675.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXjt1agu70%3D&md5=b25ff3706a92c4d9457bb01195dc840cCAS |

[2]  (a) H. Staudinger, Helv. Chim. Acta 1920, 3, 862.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaB3MXivFKg&md5=8a3835628a7d7f7c45fd040cd82b13ceCAS |
      (b) H. Kohn, P. Charumilind, Y. Gopichand, J. Org. Chem. 1978, 43, 4961.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) J. D. Coyle, P. A. Rapley, J. Kamphuis, H. J. T. Bos, J. Chem. Soc., Perkin Trans. 1 1985, 1957.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  W. Adam, H. Rebollo, R. J. Rosenthal, E.-M. Peters, K. Peters, H. G. von Schnering, Chem. Ber. 1984, 117, 2393.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2cXltlSltr4%3D&md5=e31697e8f7492e0f0ea12a232ac5f017CAS |

[4]  T. Machiguchi, S. Yamabe, Tetrahedron Lett. 1990, 31, 4169.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXmtFWjtbc%3D&md5=51c53f08a8a51b23c6fbaba5891d1d89CAS |

[5]  (a) C. Wentrup, H.-W. Winter, G. Gross, K.-P. Netsch, G. Kollenz, W. Ott, A. G. Biedermann, Angew. Chem. Int. Ed. 1984, 23, 800.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) C. Wentrup, J. J. Finnerty, R. Koch, Curr. Org. Chem. 2010, 14, 1586.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  C. O. Kappe, C. Wentrup, G. Kollenz, Monatsh. Chem. 1993, 124, 1133.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXktlGnuro%3D&md5=ef8577e7038f8c996d5a7e5321f8845eCAS |

[7]  (a) V. A. Nikolaev, A. V. Ivanov, A. A. Shakhmin, J. Sieler, L. L. Rodina, Tetrahedron Lett. 2012, 53, 3095.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XmtlWltLs%3D&md5=7eb3f53d4eb21b69b5be35f11b0df032CAS |
      (b) V. A. Nikolaev, A. V. Ivanov, A. A. Shakhmin, B. Schulze, L. L. Rodina, Russ. J. Org. Chem. 2011, 47, 1911.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  J. C. Meslin, Y. T. N’Guessan, H. Quiniou, F. Tonnard, Tetrahedron 1975, 31, 2679.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE28XktlOnsg%3D%3D&md5=e77de770b359cc6c202946fe1dc60262CAS |

[9]  (a) R. Okazaki, M. O-oka, N. Inamoto, J. Chem. Soc., Chem. Commun. 1976, 562.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2sXltlyn&md5=3078ae6c8ca8c3c45924fe82f1da700eCAS |
      (b) M. O-oka, A. Kitamura, R. Okazaki, N. Inamoto, Bull. Chem. Soc. Jpn. 1978, 51, 301.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) X. Xu, K. Wang, S. G. Nelson, J. Am. Chem. Soc. 2007, 129, 11690.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  H. Heimgartner, G. Mloston, J. Romanski, Adamantanethione, in Electronic Encyclopedia of Reagents for Organic Synthesis (Ed. L. A. Paquette) 2005, Article No. RN 00504 (Wiley: New York, NY).

[11]  (a) G. G. Qiao, J. Andraos, C. Wentrup, J. Am. Chem. Soc. 1996, 118, 5634.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28Xjt1eksbw%3D&md5=dd8bdb5d50b58679746b2046c6572ef7CAS |
      (b) P. Visser, R. Zuhse, M. W. Wong, C. Wentrup, J. Am. Chem. Soc. 1996, 118, 12598.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) G. Kollenz, S. Holzer, T. S. Dalvi, C. O. Kappe, W. M. F. Fabian, H. Sterk, M. W. Wong, C. Wentrup, Eur. J. Org. Chem. 2001, 1315.
         | Crossref | GoogleScholarGoogle Scholar |

[12]  J. W. Greidanus, Can. J. Chem. 1970, 48, 3530.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3MXjtFGrtg%3D%3D&md5=91dc9327da3331649eec22c970d689dbCAS |

[13]  (a) E. C. Taylor, A. McKillop, G. H. Hawks, Org. Synth. Coll. 1988, VI, 549.
      (b) L. I. Smith, H. H. Hoehn, Org. Synth. Coll. 1955, III, 356.