Rhodium-promoted linear tetramerization and cyclization of 3,3- dimethylbut-l-yne

Angewandte Chemie - International Edition

Volumn 38, Issue 20, 1999, Pages 3043-3045

  Burrows, Andrew D ^a   Green, Michael ^a   Jeffery, John C ^b   Lynam, Jason M ^a   Mahon, Mary F ^a  

^a University of Bath Claverton Down   (United Kingdom)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

3,3 DIMETHYLBUT 1 YNE; TETRAMER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; CYCLIZATION; METAL BINDING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC CHEMISTRY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033581545     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991018)38:20<3043::AID-ANIE3043>3.0.CO;2-2     Document Type: Article

References (33)

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23. 3].
24. [20] The asymmetric unit consists of one half of the triene-yne with the remainder generated by an inversion center, hence there is disorder between the terminal double and triple bonds.
25. It is also possible that the vinylidene complex B is formed via the hydridoacetylide complex C.
26. 3) the regiochemistry of the "insertion" step has been related to the steric demands of both the metal center and the alkyne. It is also reported in this paper that an excess of alkyne results in the formation of a palladium-trienyl species that can then undergo an intramolecular cyclization reaction to form a 5-ethylidene-2-cyclopentene-l-yl complex. Although a related intramolecular cyclization reaction with the rhodium-trienyl intermediate F (shown in Scheme 1) can be envisaged, such a process does not provide a pathway to the fulvene complex 1.
27. M. Etienne, R. Mathieu, B. Donnadieu, J. Am. Chem. Soc. 1997, 119, 3218-3228, and references therein.
28. 2H). However, in contrast with the rhodium system this occurs earlier in the oligomerization process.
29. 3].
30. 3J < 1 Hz, 1H).
31. A similar reaction has been observed on treatment of (Rh(cod)Cp] with one-electron oxidants: M. D. Kitchen, PhD thesis, University of Bristol (UK), 1978; N. G. Connelly, personal communication.
32. A similar reaction has been observed on treatment of (Rh(cod)Cp] with one-electron oxidants: M. D. Kitchen, PhD thesis, University of Bristol (UK), 1978; N. G. Connelly, personal communication.
33. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-118903 (2) and -118904 (4). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+ 44) 1223-336-033; e-mail: deposit@ccdc.cam. ac.uk).