H. Neudeck, U. H. Brinker / Tetrahedron Letters 46 (2005) 1893–1895
1895
Acknowledgements
114, 10084; (c) Jeffs, P. W.; Molina, G.; Cass, M. W.;
Cortese, N. A. J. Org. Chem. 1982, 47, 3871.
. Krepski, L. R.; Hassner, A. J. Org. Chem. 1978, 43,
9
We thank Ms. S. Felsinger, Ms. C. Tyl, and Dr. L. Brec-
ker for recording the NMR spectra, Ing. P. Unteregger
and N. Kokkotas for performing MS and GC–MS
analyses, respectively, and Mag. J. Theiner of the
Mikroanalytisches Laboratorium am Institut f u¨ r
Physikalische Chemie der Universit a¨ t Wien for
microanalyses.
2
879.
1
1
1
0. Cornejo, J. J.; Ghodsi, S.; Johnson, R. D.; Woodling, R.;
Rickborn, B. J. Org. Chem. 1983, 48, 3869.
1. Givens, R. S.; Oettle, W. F.; Coffin, R. L.; Carlson, R. G.
J. Am. Chem. Soc. 1971, 93, 3957.
2. When using DBU in an attempt to eliminate HBr from 6
(Br endo) to obtain 8, the reaction failed. By applying this
method to 12, merely 5% of a product mixture could be
isolated which consisted of 46% of 2 and 9% of 12. The
reason for the low yield should be a consequence of the
incorporated styrene-like structures which will lead to
polymerization in the very alkaline solution used. For
confirmation, pure 8 was destroyed by this procedure and
only a few percent could be recovered.
References and notes
1
2
. (a) Schiess, P.; Heitzmann, M. Angew. Chem. 1977, 89,
85; Angew. Chem., Int. Ed. Engl. 1977, 16, 469; (b)
Schiess, P.; Barve, P. V.; Dussy, F. E.; Pfiffner, A. Org.
Synth. 1995, 72, 116.
. (a) Durucasu, I.; Saracoglu, N.; Balci, M. Tetrahedron
Lett. 1991, 32, 7097; (b) M u¨ ller, P.; Bernardinelli, G.;
Jacquier, Y.; Ricca, A. Helv. Chim. Acta 1989, 72, 1618;
4
13. Compound 2: mp70–71 °C (pillar-like needles from
1
CH OH; recrystallization at 67 °C);
3
H
NMR
(400.1 MHz, CDCl ) d 4.13 (s, 1-H), 7.33 (d, J = 8.3; 3-
3
H), 7.63 (td, J = 7.1/1.8; 7-H), 7.66 (td, J = 7.1/2.0; 6-H),
7.81 (d, J = 8.3; 4-H), 7.86–7.90 (m; 8-H), 7.91–7.96 (m; 5-
(c) Abou-Teim, O.; Goodland, M. C.; McOmie, J. F. W.
J. Chem. Soc., Perkin Trans. 1 1983, 2659.
1
3
à
H); C NMR (100.6 MHz, CDCl , J-mod) d 50.0 (t; C-1),
3
3
4
5
6
. Peglion, J. -L.; Dessinges, A.; Goument, B.; Millan, M.;
Lejeune, F.; Brocco, M. Eur. Pat. Appl. 2001, 47 pp.
CODEN: EPXXDW EP 1146041 A1 20011017.
. (a) Reactive Intermediate Chemistry; Moss, R. A., Platz,
M. S., Jones, M., Jr., Eds.; Wiley: New York, 2004; (b)
Nordvik, T.; Brinker, U. H. Org. Lett. 2004, 6, 715.
. Backes, J.; Brinker, U. H. In Methoden der Organischen
Chemie (Houben-Weyl); Regitz, M., Ed.; Thieme: Stutt-
gart, 1989; Vol. E19b, pp 518–541.
117.1 (d; C-3), 125.5 (d; C-8), 127.7 (d; C-7), 128.7 (s; C-
8a), 129.4 (d; C-6), 129.7 (d; C-5), 130.5 (d; C-4), 137.0 (s;
C-4a), 144.9 (s; C-2a), 153.5 (s, C-8b), 186.2 (s; C-2); (the
assignment was done by COSY, NOESY, HMQC and
ꢀ1
HMBC); mmax/cm (ATR) 2907 (w), 1788 (m), 1746 (vst),
1627 (m), 1569 (m), 1519 (w), 1450 (m), 1414 (m), 1336
(m), 1265 (w), 1217 (m), 1167 (w), 1063 (w), 957 (m), 905
(w), 875 (w), 812 (st), 771 (m), 750 (s). m/z (EI, pot. 50 °C)
+
+
+
168 (M , 60), 140 (M ꢀ CO, 100), 139 (M ꢀ CHO, 74),
+
70 (12), 69 (14), 63 (10), (found M 168.0571 ± 5 ppm,
. Chemistry of Diazirines; Liu, M. T. H., Ed.; CRC: Boca
Raton, 1987; Vol. 1.
calcd for C H O: 168.0575). Found: C, 85.41; H, 4.99 %.
8
1
2
7
8
. Nordvik, T.; Brinker, U. H. J. Org. Chem. 2003, 68, 9394.
. (a) Dowd, P.; Zhang, W.; Geib, S. J. Tetrahedron 1995, 51,
12 8
Anal. Calcd for C H O: C, 85.69; H, 4.79%. UV
(C H OH) kmax
:
(79,000), 333 (38,500), and 345 (42,800).
250 (628,000), 275 (78,000), 284
2
5
3
435; (b) Dowd, P.; Zhang, W. J. Am. Chem. Soc. 1992,
Bruker Avance DRX-400 spectrometer [CHCl
Bruker Avance DRX-400 spectrometer [CDCl
3
3
set at 7.24 ppm].
set at 77.00 ppm].
à