Isomerizations in the dicyclopentadiene series

✍ Scribed by P. Yates; P. Eaton

• Book ID: 104236232
• Publisher: Elsevier Science
• Year: 1960
• Tongue: French
• Weight: 193 KB
• Volume: 1
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)84070-3

✦ Synopsis

RECENT interest in the thermal rearrangement of dicyclopentadiene alcohols' and in the chemistry of related polychloroketonee2 leads us to give a preliminary report on experiments concerned with the isomerization of 4,5,6,7tetrachlaro-ja,4,7,7a-tetrahybro-4,7-methanoinden-8-one (I), m.p. l23-l23.5', X24 3.34, 5.48, 6.33 CI (P ound: C, 42.32; H, 2.05; Cl, 49.86. CloH6C140 requires: C, 42.29; H, 2.13; Cl, 49.94), prepared by hydrolysis of the adduct (II)3 from cyclopentadiene and 1,2,3,4-tetrachloro-5,5-diethoxycyclopentadiene. When I was heated at 135' for 1 hr it was converted in quantitative yield to an isomer, m.p. 82-83', h_ ccl4 3,239 3.31, 5.73, 6.30 PL, XE 255 IQ.I (E 9100) (Found: C , 42.53; H, 2.14, Cl, 49.86). This is formulated as III on the basis of the spectral data and its conversion to IV, m.p. 202-203' (sealed aap.), h_ "'4 5. 28, 5.36, 5.53 p (Pound: C, 46.04; H, 3.67; Cl, 29.89. CgH8C1203 requires C, 45.981 H, 3.43; Cl, 30.17), which was shown to be identical with the product obtained by hydrogenation of the ' R.B. Woodward and T.J. Katz, Tetrahedron 2, 70 (1959).