References
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- Recently we have carried out extensive studies for diacylation of active methylenes with the help of solid-liquid biphasic catalyst. This work forms partially the projected thesis of Mr. S.N. Naik. Such reactions are quite uncommon in PTC chemistry. See the preceding communication in this issue
- Physical and spectroscopic data for 4, 9, and 10 are as follows. 4: m.p. 152°C, IR (CCl4): 2950 cm−1 (s), 1800 (s), 1780 (s), 1650 (w); 1H-nmr (CDCl3): 7.0δ (d, 1H, J = 8Hz), 7.2δ (d, 1H, J = 8Hz), 7.75–8.5δ (m, 8H); 13C-nmr (CDCl3): 73.90 (s), 121.43, 123.69, 125.10, 121.51, 126.04, 126.26, 127.01, 128.17, 130.62, 131.22, 134.76, 135.63, 142.28 and 212.9 (s); MS: [EI, M+ (relative intensity %)]: 246 (M+, 70), 218(30), 189(100), 167(28), 149(25), 69(30). 9: Yellow needles, m.p. 192°C: IR (CHCl3): 1790 (s), 1780 (s), 1645 (w); 1H-nmr (CDCl3): 7.0–7.44 (m, 2H), 7.77–8.44 (m, 8H); 13C-nmr (CDCl3): 121.41, 123.67, 124.60, 125.20, 125.49, 126.18, 128.14, 130.64, 131.16, 134.73, 135.86 and 162.56 (s); MS: [EI, M+ (relative intensity %)]: 246(100), 218(30), 189(50), 114(15), 76(15). Structure was confirmed by X-ray as well. 10: Brown needles, m.p. 320°C (decomp.); IR (CHCl3): 1790 (s), 1780 (s), 1620 (m); 1H-nmr (CDCl3): 6.88–7.17 (m, 2H, vinylic), 7.28–7.51 (m, 3H, aromatic), 7.60–7.77 (m, 2H, aromatic), 8.0–8.44 (m, 2H, aromatic), 8.57–8.78 (m, 1H, aromatic); MS: [EI, M+ (relative intensity %)]: 246(100), 218(40), 189(70), 114(40), 94(35), 76(20)
- Two carbonyl frequencies for cyclic 1,3-diones are generally observed in IR;
- A careful analysis of molecular ion peaks intensities in MS in various model spiro compounds prepared in Ref. 2, showed that it is quite prominent
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