HETEROCYCLES, Vol. 82, No. 1, 2010
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Hz), 5.81 (m, CH=CH-CHP, 1H). C NMR (75.5 MHz, CDCl3, Me4Si): (d, JPC = 4.9 Hz),
21.5, (d, 2JPC = 7.9 Hz), 42.2,43.1 (d, 1JPC = 160.0 Hz),60.9 (d, 2JPC = 8.1 Hz), 129.0, 136.2 (d,
2JPC = 8.0 Hz), 176.7, 177.4. 31P NMR (125 MHz, CDCl3, Me4Si): 31.55. MS (EI): m/z (%) 79.0 (36.0),
91.0 (100), 105.0 (85.0), 125.0 (94.0), 152.0 (59.0), 173.0 (31.0), 187.0 (22.0), 201.0 (28.0), 229.0 (69.0),
316.0 (11.0). Anal. Calcd for C14H21O6P: C, 53.16; H, 6.69; P, 9.79. Found: C, 53.11; H, 6.68; P, 9.78.
Diethyl 7-methyl-1,3-dioxo-1,3,3a,4,7,7a-hexahydroisobenzofuran-4-ylphosphonate (4b). Identical to
4a. 1H NMR (300 MHz, CDCl3 , Me4Si): CH3CHdJHH = 7.3 Hz), 1.28 (6H, OCH2CH3, t, JHH
= 7.3 Hz), 2.25 (1H, CH3CHCHCO, dd, JHH = 7.6 Hz, JHH = 4.9 Hz), 2.52 (1H, CH3CH, m), 3.43 (1H,
COCHCHP, m), 3.50 (1H, CHP, m), 4.07 (4H, OCH2CH3, m), 5.64 (1H, CH3CH-CH=CH, dd, JHH = 6.8 Hz,
J
HH = 4.6 Hz), 5.83 (CH=CH-CHP, H2 m). 13C NMR (75.5 MHz, CDCl3 , Me4Si): (d, 3JPC = 5.6
Hz), (d, 2JPC = 8.6 Hz), 40.1,40.7 (d, 1JPC = 145.9 Hz),62.2 (d, 2JPC = 8.6 Hz), 128.2, 133.1 (d,
2JPC = 7.1 Hz), 172.3, 173.4. 31P NMR (125 MHz, CDCl3, Me4Si): 29.20. MS (EI): m/z (%) 51.0 (14.9),
77.0 (63.3), 91.0 (100), 109.0 (97.0), 119.0 (33.7), 138.0 (92.1), 155.0 (19.8), 173.0 (11.9), 302.0 (10.9).
Anal. Calcd for C13H19O6P: C, 51.66; H, 6.34; P, 10.25. Found: C, 51.61; H, 6.33; P, 10.24.
Diethyl 7-dodecyl-1,3-dioxo-1,3,3a,4,7,7a-hexahydroisobenzofuran-4-ylphosphonate (4c). Identical to
4a. 1H NMR (300 MHz, CDCl3, Me4Si): CH3CHtJHH = 7.4 Hz), 1.24 (6H, OCH2CH3, t, JHH
= 7.7 Hz), 1.26-1.36 (20H, CH3(CH2)10CH2, overlap), 1.31 (2H, CH2CH2CH, m) 2.26 (1H, CH2CHCHCO,
dd, JHH = 8.1 Hz, JHH = 4.7 Hz), 2.50 (1H, CH2CH, m), 3.36 (1H, COCHCHP, m), 3.44 (1H, CHP, m), 4.08
(4H, OCH2CH3, m), 5.63 (1H, CH2CH-CH=CH, dd, JHH = 6.4 Hz, JHH = 5.0 Hz), 5.82 (1H, CH=CH-CHP,
m). 13C NMR (75.5 MHz, CDCl3, Me4Si): (d, 3JPC = 5.1 Hz), 21.3, 21.4,
(d, 2JPC = 8.0 Hz), 36.6, 44.4,45.1 (d, 1JPC = 159.9 Hz),61.6 (d, 2JPC = 8.7 Hz), 128.7,
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136.8 (d, JPC = 8.4 Hz), 171.5, 171.8. P NMR (125 MHz, CDCl3, Me4Si): 30.83. MS (EI): m/z (%)
163.0 (75.2), 178.1 (59.6), 191.1 (100), 205.1 (35.8), 219.1 (45.0), 233.2 (42.2), 247.2 (31.2), 261.2 (27.5),
275.3 (23.9), 303.4 (20.2), 331.5 (23.9), 360.7 (43.1), 411.4 (2.1), 456.2 (0.1). Anal. Calcd for C24H41O6P:
C, 63.14; H, 9.05; P, 6.78. Found: C, 63.05; H, 9.04; P, 6.77.
Diethyl 7-decyl-1,3-dioxo-1,3,3a,4,7,7a-hexahydroisobenzofuran-4-ylphosphonate (4d). Identical to
1
4a. H NMR (300 MHz, CDCl3, Me4Si): CH3CHtJHH = 8.4 Hz), 1.23-1.34 (16H,
CH3(CH2)8CH2, overlap), 1.27 (6H, OCH2CH3, t, JHH = 8.2 Hz), 1.30 (2H, CH2CH2CH, m) 2.26 (1H,
CH2CHCHCO, dd, JHH = 8.2 Hz, JHH = 5.0 Hz), 2.52 (1H, CH2CH, m), 3.33 (1H, COCHCHP, m), 3.44 (1H,
CHP, m), 4.08 (4H, OCH2CH3, m), 5.63 (1H, CH2CH-CH=CH, dd, JHH = 6.3 Hz, JHH = 5.1 Hz), 5.78 (1H,
CH=CH-CHP, m). 13C NMR (75.5 MHz, CDCl3, Me4Si): (d, 3JPC = 5.2 Hz), 22.5,