This work was supported by CNRS, MRES, and ANR
BLAN ‘‘Allenes’’ 06-2_159258. LF and MM are members of
Institut Universitaire de France.
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5 On the other hand, allenynes can be cycloisomerised into vinyl
´
allenes, see: (a) N. Cadran, K. Cariou, G. Herve, C. Aubert,
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y Experimental procedure: (acetonitrile)[(2-biphenyl)di-tert-butyl-
phos-phine]gold(I) hexafluoroantimonate (Aldrich, 11 mg) was added
to a solution of 1e (200 mg) in anhydrous DCM (0.025 M). The
reaction progress was monitored by TLC. When the reaction was
complete (ca. 12 h of stirring at rt), the mixture was filtered through a
short pad of silica. The solvent was removed under vacuum, and the
crude was purified by flash chromatography to afford 2e (142 mg, 71%
yield) as a colourless oil. IR (neat): n = 2954, 1732, 1433, 1243,
898 cmꢁ1. 1H NMR (400 MHz, CDCl3) d 6.13 (dt, J = 17.2, 10.0, 1 H);
5.85 (m, 1 H); 5.14 (dd, J = 17.0, 4.0, 1 H); 4.94 (dd, J = 10.0, 6.8,
1 H); 3.73 (m, 6 H); 3.03–2.92 (m, 2 H); 2.66 (m, 1 H); 2.43
(dd, J = 12.8, 7.6, 1 H); 1.89 (q, J = 12.0, 1 H); 1.76 (m, 1 H);
0.94–0.83 (m, 6 H). 13C NMR (100 MHz, CDCl3) d 201.3 (2 C), 171.8
(4 C), 133.4 (2 C), 115.2 (2 C), 104.7 (2 C), 97.0 (2 C), 59.0 (2 C),
52.7 (4 C), 47.7 (2 C), 38.9 (2 C), 35.8 (2 C), 29.8 (2 C), 20.6 (2 C), 18.1
(2 C). HRMS (ES+) calculated for C16H22O4 (M+Na): 301.1411;
found 301.1405.
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10 Although 1,2-hydride shifts are very common, longer-range
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ꢀc
This journal is The Royal Society of Chemistry 2010
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