N. Kishorebabu, M. Periasamy / Tetrahedron Letters 47 (2006) 2107–2109
. Weidenmuller, H.-L.; Cavagna, F.; Fehlhaber, H.-W.;
2109
Cl
4
5
was then cooled to 0 ꢁC and a saturated aqueous NH
4
Prave, P. Tetrahedron Lett. 1972, 13, 3519–3522.
. (a) Heck, R. F. J. Am. Chem. Soc. 1972, 94, 2712–2716; (b)
Zargarian, D.; Alper, H. Organometallics 1991, 10, 2914–
solution (10 mL) was added and the contents were stirred
for 0.5 h. The organic layer was separated and the aqueous
2 2
layer was extracted with CH Cl (2 · 25 mL). The com-
2
921; (c) Li, J.; Li, G.; Jiang, H.; Chen, M. Tetrahedron
bined organic extract was washed with 2 N HCl (10 mL),
water (10 mL), brine solution (10 mL) and dried over
anhydrous Na SO . The solvent was evaporated and the
Lett. 2001, 42, 6923–6924; (d) Sakurai, Y.; Sakaguchi, S.;
Ishii, Y. Tetrahedron Lett. 1999, 40, 1701–1704; (e)
Gabriele, B.; Salerno, G.; Costa, M.; Chiusoli, G. P.
Tetrahedron Lett. 1999, 40, 989–990; (f) Gabriele, B.;
Salerno, G.; Costa, M.; Chiusoli, G. P. Chem. Commun.
2
4
residue was chromatographed on a silica gel column.
Phenyl maleic anhydride 1a (92% yield) was collected
using EtOAc/hexane (4:96) mixture as an eluent.
1
3
1
999, 1381–1382; (g) Gabriele, B.; Veltri, L.; Salerno, G.;
Costa, M.; Chiusoli, G. P. Eur. J. Org. Chem. 2003, 1722–
728.
11. Physical constants,
C NMR and mass spectral
5
g
data: Compound 1a: mp: 117–118 ꢁC (lit. 118–119 ꢁC),
1
3
1
C NMR d ppm: 164.5, 163.6, 146.8, 132.7, 129.3, 129.0,
5g
6
. Periasamy, M.; Rameshkumar, C.; Mukkanti, A. J.
Organomet. Chem. 2002, 649, 209–213, and references
cited therein.
126.9, 124.5. Compound 1b: mp: 105–106 ꢁC (lit. 106–
108 ꢁC), C NMR d ppm: 164.6, 163.8, 146.6, 143.8,
130.1, 129.0, 124.2, 123.1, 21.6. Compound 1c: mp: 141–
143 ꢁC (lit. 142–143 ꢁC), C NMR d ppm: 165.2, 163.3,
159.2, 146.4, 131.1, 128.6, 121.0, 114.9, 55.8. Compound
1d: mp: 98–100 ꢁC, C NMR d ppm: 166.1, 164.8, 139.9,
138.7, 130.9, 129.4, 128.9, 127.5, 10.7, MS (EI): m/z 188
(M ). Compound 1e: mp: 108–110 ꢁC, C NMR d ppm:
166.4, 165.0, 141.6, 139.8, 137.6, 129.7, 129.4, 128.7, 21.5,
13
5
g
13
7
8
9
. Periasamy, M.; Rao, V. D. Tetrahedron: Asymmetry 1999,
1
1, 1151–1155.
1
3
. Periasamy, M.; KishoreBabu, N.; Jayakumar, K. N.
Tetrahedron Lett. 2003, 44, 8939–8941.
. Periasamy, M.; Suresh, S. Tetrahedron Lett. 2004, 45,
+
13
6
291–6293.
+
1
0. Representative procedure for the synthesis of maleic
anhydrides: 1,2-Dichloroethane (25 mL), ethyl benzoyl-
formate (0.75 mL, 5 mmol) and acetic anhydride
10.9, MS (EI): m/z 202 (M ). Compound 1f: mp 119–
120 ꢁC, C NMR d ppm: 172.2, 166.5, 164.7, 161.7, 139.7,
131.3, 128.9, 114.5, 55.4, 10.9, MS (EI): m/z 218 (M ).
1
3
+
1
2
13
(
0.94 mL, 10 mmol) were stirred together at room tem-
perature under N . TiCl (2.2 mL of a 1:1 solution of
TiCl /CH Cl , 10 mmol) and n-Bu N (1.4 mL, 6 mmol)
were added. The reaction mixture was refluxed for 12 h. It
Compound 2a: mp 157–159 ꢁC (lit. 159–162 ꢁC),
C
2
4
NMR d ppm: 164.8, 138.1, 131.1, 129.7, 128.9, 127.1.
4
2
2
3
12. Raghavan, P. V.; Srinivas, P.; Rao, V. V.; Manojit, P.;
Rao, Y. K. Synlett 2002, 947–951.