Heck Reaction: Stereo Selective Synthesis of Trisubstituted Olefins: Useful Intermediates for Anthraquinone Carboxylic Acid Derivatives

References

• Heck , R. F. 1968 . J. Am. Chem. Soc. , 90 : 5518
   Web of Science ®Google Scholar
• De Meijere , Armin and Meyer , Frank E. 1994 . Angew. Chem. Int. EdEng. , 33 : 2379
   Web of Science ®Google Scholar
• Miyayura , Norio and Suzuki , A. 1979 . J. C. S. Chem. Commun. , 866
   Google Scholar
• Agrios , Konstantinos A. and Morris , Srebnik . 1993 . J. Org. Chem. , 15 : 444
   Google Scholar
• Gallagher , Peter T. , Terry , Hicks A. , Light Foot , Andrew P. and Owton , W. M. 1994 . Tet. Lett. , 35 ( 2 ) : 289
   Web of Science ®Google Scholar
• Owton , W. M. 1994 . J. C. S. Perkin Trans. , : 1
   Google Scholar
• Gallagher , P. T. , Hick , T. A. and Owton , W. M. Eur. Pat. Appl. EP . 638, 540 CI. 02 C07C66/15 . Feb. 1995 . CA 122:213773 d.
   Google Scholar
• Gallagher , P. T. , Hick , T. A. and Owton , W. H. Eur. Pat. Appl. EP . 638, 562, CI C07D257/04 . 15 Feb. 1995 . CA 122;214082q
   Google Scholar
• Yashida , J. , Tamao , K. , Yamamoto , H. , Kakui , T. , Uchida , T. and Kumada , M. 1982 . Organometallics , 3 : 542
   Google Scholar
• Hannan , R. L. , Barben , R. B. and Rappaport , H. 1979 . J. Org. Chem. , 44 : 2153
   Web of Science ®Google Scholar
• Alternatively 1‐methoxy 5‐naphthol was also prepared in 40 % yield starting from 1,5‐dihroxynaphthalene and 0.5 eq. of Mel/acetone, K2CO3atRTforl0hrs
   Google Scholar
• Carter , A. H. , Race , E. and Rawe , F. M. 1942 . J. Chem. Soc , : 236
   Google Scholar
• Jung , M. E. and Hagenah , J. A. 1987 . J. Org. Chem. , 52 : 1889
   Web of Science ®Google Scholar
• C3‐methylene hydrogens and 3′H of aryl moiety in all the products showed NOE relationship
   Google Scholar
• Compound 13: m.p 212oC 1. H NMR (200 MHz, CDCI3 δ 1.3 (3H, t) 3.68 (2H, s), 4.05 (3H, s), 4.25 (2H, q), 7.0 ( 1H, d), 7.45 ( 1H, d), 7.58 ( 1H, t), 7.85 (1H, s), 8.15 ( 2H, d). EIMS m/z 312 (100%)
   Google Scholar
• Harvey , Ronald G. , Ananthanarayan , Cecilia Cortez and Schmolka , Sanford . 1988 . J. Org. Chem. , 53 : 3936
   Web of Science ®Google Scholar
• Compd. 7: 1. H NMR (200 MHz, CDC13) δ 1.3 (6H, m), 3.4 (2H, s), 3.75 (3H, s), 4.25 (4H, m), 6.91–7.3 (4H, m). EIMS: m/z 292 (M+, 100%). Compd. 8: 1. H NMR (400 MHz, CDCI3) δ 1.22 (3H, q), 1.26 (3H, q), 3.42 (2H, s), 3.74 (3H, s), 3.79 (3H, s), 4.19 (2H, q), 4.28 (2H, q), 6.84 (3H, m), 7.9 (1H, s). EIMS: m/z 322 (M+‐, 100%). Compd. 9: 1. H NMR (400 MHz, CDCI3) δ1.2 (3H, t), 1.3 (3H, t), 3.26 (2H, s), 3.81 (3H, s), 3.9 (3H, s), 4.1 (2H, q), 4.22 (2H, q), 6.66 (1H, d), 6.81 (1H, d), 7.18 (1H, d), 7.26 (1H, t), 7.82 (1H, d), 8.58(1H, s). EIMS: m/z 372 (M+ 100 %) Compd. 11: 1. NMR (200 MHz, CDCI3) δ 1.27 (6H, m), 3.55 (2H, s), 4.05 (3H, s), 4.2 (4H, m), 5.04 (2H, s), 6.96–8.1 (10H, m), 8.2 (1H, s). EIMS: m/z 448 (M+, 5%)
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• The Melting Point of the acids from the esters 7,8, 9 and 11 are 95oC, 98oC, 208oC and 145oC respectively
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