138
Z. Grobelny et al. / Journal of Organometallic Chemistry 660 (2002) 133Á138
/
water bath for 3 h. After cooling 100 cm3 water and 100
cm3 hexane have been added. The layers have been
separated, the organic layer has been washed three times
with 20 cm3 water and dried with anhydrous MgSO4.
Volatile constituents (mostly hexane and toluene) have
been removed by distillation on a rotatory evaporator.
The residue has been distilled under reduced pressure.
Finally, 6-allyloxy-5-benzyloxy-1-hexene has been ob-
4.7. Benzyl phenyl ether (19)
Its 1H-, 13C-NMR and mass spectra were described in
[2].
Tri- and tetraethylene glycol dimethyl ethers. Their
1H-, 13C-NMR and mass spectra were described in [3].
To the best of our knowledge two of these com-
pounds, i.e. 1-butoxy-2-benzyloxypropane (7) and 6-
allyloxy-5-benzyloxy-1-hexene (16) were till now not
described in the literature.
tained in 70% yield. B.p.ꢂ
/
118 8C per 1 mmHg. 13C-
NMR CDCl3 d:
Acknowledgements
The authors are indebted to Dr. G. Adamus and Dr.
K. Skutil for GC analysis of liquid and gaseous reaction
products. This work was supported by the Committee of
Scientific Research in Poland (project No. 3 TO9A 097
18).
1H-NMR CDCl3 d 7.38Á
1H, ÃOÃCH2ÃCH ÄCH2, Jꢂ
5.5 Hz); 5.771 (ddt, 1H, CH2Ä
16.8 Hz, Jꢂ10.2 Hz, Jꢂ6.6 Hz); 5.254 (dtd, 1H, Ã
OÃCH2ÃCHÄCH2-cis, Jꢂ17.2 Hz, Jꢂ1.4 Hz, Jꢂ
1.3 Hz); 5.142 (dtd, 1H, ÃOÃCH2ÃCHÄCH2-trans,
Jꢂ10.6 Hz, Jꢂ1.8 Hz, 1.3 Hz); 4.983 (dtd, 1H, cis-
CH2ÄCHÃCH2ÃCH2Ã, Jꢂ16.8 Hz, Jꢂ1.8 Hz, Jꢂ1.4
Hz); 4.931 (dtd, 1H, trans-CH2ÄCHÃCH2ÃCH2Ã, Jꢂ
10.2 Hz, Jꢂ1.8 Hz, 1.3 Hz); 4.664, 4.521 (qAB, 2H,
PhÃCH2Ã, JAB 11.7 Hz); 3.956 (ddd, 2H, ÃOÃCH2Ã
CHÄCH2, Jꢂ5.5 Hz, Jꢂ1.8 Hz, Jꢂ1.4 Hz); 3.557
(dddd, 1H, CH2ÄCHÃCH2ÃCH2ÃCH Ã, Jꢂ7.6 Hz,
Jꢂ5.8 Hz, Jꢂ4.5 Hz, Jꢂ4.3 Hz); 3.493 (dd, 1H, Ã
CHÃCH2ÃOÃ, Jgem 10.1 Hz, Jꢂ5.8 Hz); 3.438
(dd, 1H, ÃCHÃCH2ÃOÃ, Jgem 10.1 Hz, Jꢂ4.3
Hz); 2.183 (ddddd, 1H, CH2ÄCHÃCH2ÃCH2Ã
Jgem 14.7 Hz, Jꢂ6.8 Hz, Jꢂ6.6 Hz, Jꢂ1.8 Hz,
Jꢂ1.4 Hz); 2.100 (ddddd, 1H, CH2ÄCHÃCH2ÃCH2Ã
Jgem 14.7 Hz, Jꢂ7.3 Hz, Jꢂ6.6 Hz, Jꢂ1.8 Hz,
Jꢂ1.4 Hz); 1.634 (ddd, 1H, CH2ÄCHÃCH2ÃCH2Ã
Jgem 13.6 Hz, Jꢂ7.6 Hz, Jꢂ7.3 Hz); 1.611 (ddd,
1H, CH2ÄCHÃCH2ÃCH2Ã, Jgem 13.6 Hz, Jꢂ6.8
Hz, Jꢂ
4.5 Hz). MS m/z (%) 246 [Mꢁ, 2], 188 (2), 175
/
7.18 (m, 5H, PhÃ
17.2 Hz, Jꢂ
CH ÃCH2Ã
/
); 5.873 (ddt,
10.6 Hz, Jꢂ
CH2Ã, Jꢂ
/
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