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metathesis products are as follows. Compound 6: To a
stirring solution of diene 5 (50 mg, 0.10 mmol) in dry
CH2Cl2 (8 ml) was added a solution of catalyst 1 (4 mg,
0.005 mmol) in dry CH2Cl2 (2 ml). The reaction mixture
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added a solution of catalyst 2 (5 mg, 0.006 mmol) in dry
CH2Cl2 (2 ml). The reaction mixture was stirred for 20 h
at room temperature under an N2 atmosphere, then the
solvent was removed in vacuo and the residue subjected to
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Compound 9: To a stirring solution of compound 8
(50 mg, 0.10 mmol) in dry CH2Cl2 (8 ml) was added a
solution of catalyst 1 (8 mg, 0.010 mmol) in dry CH2Cl2
(2 ml). The reaction mixture was stirred for 20 h at 35 °C
under an N2 atmosphere, then the solvent was removed in
vacuo and the residue subjected to chromatography
(CH2Cl2/EtOAc 98:2) to afford diene 9 (28 mg, 56%) as
a white solid (mp 165–167 °C). Compounds 12 and 13:
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CH2Cl2 (16 ml) and ethene was passed through the stirred
solution for 20 min. A solution of catalyst 1 (17 mg,
0.021 mmol) in dry CH2Cl2 (5 ml) was then added and the
reaction mixture was stirred at room temperature for 20 h
under an ethene atmosphere. The solvent was then
removed in vacuo and the residue purified by chromato-
graphy (CH2Cl2/EtOAc 96:4) to give compound 12 (17 mg,
16%) as a white solid (mp 182 °C dec) and compound 13
(67 mg, 63%) as a transparent oil. Compound 19: Diyne 18
(100 mg, 0.2 mmol) was dissolved in dry CH2Cl2 (17 ml)
and ethene was passed through the stirred solution for
20 min. A solution of catalyst 1 (8 mg, 0.010 mmol) in dry
CH2Cl2 (3 ml) was then added and the reaction mixture
was stirred at room temperature for 20 h under an ethene
atmosphere. The solvent was then removed in vacuo and
the residue subjected to chromatography (CH2Cl2/EtOAc
95:5) to give compound 19 (45 mg, 43%) as a transparent
oil.
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