S. Elgafi et al. / Journal of Organometallic Chemistry 607 (2000) 97–104
103
Acknowledgements
The product, 2-methyl-2-(4-pentynyloxy)-3,4,5-trihy-
drofuran (14), was formed in 19% conversion from
starting material [35]. H-NMR (600 MHz, acetone-d6):
1
We gratefully acknowledge financial support from
the Australian Research Council. We also thank John-
son Matthey Pty. Ltd. for the generous loan of iridium
and rhodium salts.
l 3.87–3.81 (m, 2H, H5A, H5B), 3.56–3.51 (m,
1H, OCHAHB), 3.51–3.45 (m, 1H, OCHAHB), 2.30–
2.28 (m, 1H, CꢂCH), 2.27 (m, 2H, CH2CꢂCH), 2.07–
2.01 (m, 1H, H4B), 2.01–1.96 (m, 1H, H3B), 1.91–1.85
(m, 1H, H4A), 1.75–1.68 (m, 1H, H3A), 1.73–1.68
(m, 2H, CH2CH2CꢂCH), 1.40 (s, 3H, CH3). 13C{1H}-
NMR (100 MHz, acetone-d6): l 106.9 (C2), 83.7
(CꢂCH), 68.7 (CꢂCH), 66.9(C5), 58.6 (OCH2), 37.8
(C3), 29.5 (OCH2CH2), 24.3 (C4), 21.3 (CH3), 14.8
(CH2CꢂCH).
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4.7.2. Catalysed by
[{Rh((mBnzim)2CH2)(CO)2}+BPh−4 ] (2)
4-Pentyn-1-ol (180 mg, 2.1 mmol) was added to a
solution of [{Rh((mBnzim)2CH2)(CO)2}+BPh4−] (2) (13
mg, 0.017 mmol) in acetone-d6 (0.3 ml) in a NMR tube.
The mixture was heated at 60°C in an oil bath for 4 h.
The product, 2-methyl-2-(4-pentynyloxy)-3,4,5-trihy-
drofuran (14), was formed in 30% conversion from
starting material [35].
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(1)
cis-3-Methyl-2-pentene-4-yn-1-ol (155 mg, 1.61
mmol) was added to a solution of [{Rh((mim)2CH2)-
(CO)2}+BPh4−] (1) (3.7 mg, 5.4 mmol) in acetone-d6 (0.3
ml) and benzene (0.4 g, internal standard) in a NMR
tube. The mixture was heated at 50°C for 26.5 h. The
product 2,3-dimethylfuran (15) was formed in 93%
conversion from starting material [1,36]. Spectroscopic
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1
data were consistent with literature data [31]. H-NMR
3
(400 MHz, acetone-d6): l 7.30 (d, 1H, JH5ꢀH4=1.9 Hz,
3
H5), 6.21 (d, 1H, JH5ꢀH4=1.9 Hz, H4), 2.20 (s, 3H,
C(2)CH3), 1.96 (s, 3H, C(3)CH3).
13C{1H}-NMR (100 MHz, acetone-d6): l 146.9 (C2),
139.6 (C5), 113.5 (C3), 112.6 (C4), 10.2 (C2ꢀCH3), 8.8
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4.8.2. Catalysed by
[{Rh((mBnzim)2CH2)(CO)2}+BPh−4 ] (2)
cis-3-Methyl-2-pentene-4-yn-1-ol (90 mg, 0.94 mmol)
was added to a solution of [{Rh((mBnzim)2CH2)-
(CO)2}+BPh4−] (2) (4.8 mg, 6.1 mmol) in acetone-d6 (0.3
ml) and benzene (0.4 g, internal standard) in a NMR
tube. The mixture was heated at 50°C for 21.5 h. The
product 2,3-dimethylfuran (15) was formed in 60%
conversion from starting material [36].