1,5-HYDROGEN SHIFT IN A DECAHYDRODIMETHANONAPHTHALENE SYSTEM¹

Stereochemistry of the Diels-Alder Reaction.

“…The reasonable assumption was made that the adducts of norbornene and acetoxynorbornene have the same stereochemistry; this has since been verified by Stille and Frey (275), who related the cyclopentadiene-norbornadiene adduct (LXI) to both Soloway's adduct and the adducts prepared by Alder. Hexachlorocyclopentadiene adds to 7-anif-hydroxynorbornene to afford an adduct of the same skeletal configuration (299).…”

Formation of endo acetate in acetolysis of a fused endo-norbornyl brosylate via C-7 participation

“…All the pentane washings and extracts were combined, washed with water, dried (Na2S04), and concentrated. The residual white solid was sublimed at 80°( 1 mm) to give 9.0 g (41% from the crude diene) of solid, mp 94-96°( lit.7 mp 90-92), that was 99.3% endo.endo diene and 0.7% endo.endo monoene (gc analysis on a 25% SE-30 on Chromosorb W colunn26): ir (CC14) 3.21 (w), 3.30 (m), 3.41 (s), 3.52 (m), 6.39 (w), 6.90 (m), 7.49 (s), 7.88 (w), 8.00 (s), 8.11 (w), 8.20 (w), 8.85 (m), 9.12, (w), 9.71 (w), 10.13 (w), 10.35 (w), 10.99 (s), 11.31 (a), 11.45 (s), 14.00 (vs), 14.50 µ (w).…”

Sterische Effekte bei endo, exo ‐Tetracyclo[6.2.1.1 3,6. 0 2,7 ]‐dodecanen: Einfluß von 4‐Substituenten auf die Solvolyse der 11‐epimeren Sulfonate 1)

“…13.6.d. 'Idodecan-1 I-anti-ol (6s): 0.70 g 13 b -IR: 3628, 3024, 2951-IR: 3628, 3024, , 2910-IR: 3628, 3024, , 1455-IR: 3628, 3024, , 1372-IR: 3628, 3024, , 1290-IR: 3628, 3024, , 1130-IR: 3628, 3024, , 1080 (17), 150(32), 131 (13), 119 (26), 94 (13), 93(35), 91 (29), 77 (23), 67 (32), 55 (19). 41 (41).…”

“…-IR: 3083, 3063, 3028, 2954, 2912, 2872, 1730, 1490, 1365, 1245, 1235, 1095, 1038 crn-'. - (13), 178(11), 174(16), 160(26), 150(20), 132 (13), 131 ( l l ) , 123 (15), 121 ( l l ) , 119 (13), 111 (13), 109 (22), 108 (53), 107 (26). 93 (22), 92 (76), 91 (100).…”

“…-IR: 3626, 3086, 3064, 3030, 2949, 2907, 2874, 1605, 1585, 1460, 1365, 1135, 1105, 1080, 735 cm-'. - (18), 121 (13), 119 (26), 93 (14), 92 (27), 91 (100).…”