FULL PAPERS
Antonio Procopio et al.
(
100); anal. calcd. for C H O : C 63.53, H 8.23; found: C 63.29,
[12] I. Busci, A. Meleg, A. Molnar, M. Bartok, J. Mol. Catal.
2001, 168, 47–52.
9
14
3
H 8.33.
[
13] R. D. Adams, T. S. Barnard, K. Brosius, J. Organomet.
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Spiro[5,4]7,10-dioxa-8-butyldecane (9)
[14] N. Iranpoor, F. Kazemi, Synth. Commun. 1998, 28, 3189–
193.
3
1
H NMR (CDCl ): d¼0.90 (t, 3H, CH , J¼6.86 Hz), 1.30–1.40
3
3
[
[
[
[
15] I. Mohammadpoor-Baltork, A. Khosropour, H. Aliyan,
(
m, 2H), 1.57–1.64 (m, 2H), 1.67–1.78 (m, 8H), 1.82–1.92 (m,
Synth. Commun. 2001, 31, 3411–3416.
16] H. Firouzabadi, N. Iranpoor, H. Shaterian, Bull. Chem.
Soc. Jpn. 2002, 75, 2195–2205.
17] S. Tangestaninejad, M. Habibi, V. Mirkhani, M. Mogha-
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18] M. Habibi, S. Tangestaninejad, V. Mirkhani, B. Yadolla-
hi, Catal. Lett. 1975, 3–4, 205–207.
4
H), 3.49 (t, 1H, H , J¼6.88 Hz), 4.10–4.00 (m, 2H, H H );
a’
a
b
anal. calcd for C H O : C 72.73, H 11.11; found: C 72.66, H
12
22
2
10.98.
Methyl 2,3-Anhydro-a-d-mannopyranoside (7)
1
H NMR (CDCl ): d¼3.13 (d, 1H, H-3, J
¼3.70 Hz), 3.32
[19] J. R. Vyvyan, J. A. Meyer, K. D. Meyer, J. Org. Chem.
2003, 68, 9144–9147.
[20] a) R. Dalpozzo, A. De Nino, L. Maiuolo, M. Nardi, A.
Procopio, A. Tagarelli, Synthesis 2004, 496–498; b) A.
Procopio, R. Dalpozzo, A. De Nino, L. Maiuolo, B. Rus-
so, G. Sindona, Adv. Synth. Catal. 2004, 346, 1465–1470.
3
H3,H2
(
(
1
d, 1H, H-2, J
¼3.70 Hz), 3.46 (s, 3H, OCH ), 3.50–3.65
H2,H3
3
m, 1H, H-5), 3.78 (t, 2H, H-6, JH6,H5 ¼3.98 Hz), 3.87 (d,
H, H-4, JH4,H3 ¼9.19 Hz), 4.89 (s, 1H, H-1); anal. calcd. for
C H O : C 47.73, H 6.82; found: C 47.51, H 6.69.
7
12
5
[
21] A 0.1 M water solution of Er(OTf) is only weakly acidic
3
References and Notes
(pH ca. 5.9), and the aqueous layer from work-up is even
less acidic (pH ca. 6.6).
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[
[
2
3
1450
ꢀ 2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
asc.wiley-vch.de
Adv. Synth. Catal. 2005, 347, 1447–1450