ChemInform Abstract: CONTRASTING REACTIONS OF SILVER PERCHLORATE AND SILVER TOSYLATE WITH 6‐ENDO‐HYDROXY‐5‐EXO‐IODONORBORN‐2‐ENDO‐YLACETIC ACID Δ‐LACTONE

Abstract

Die Umsetzung des Iodlactons (III) mit Silberperchlorat in Benzol führt in einer raschen Reaktion zum gewünschten Lacton (I) und dem Ether (II), während die Reaktion mit Silbertosylat in Acetonitril zu (I) sehr langsam verläuft und als Nebenprodukt das Tosylat (IV) liefert.

The reactions of norbornyl-type cations derived from the reaction of silver toluene-4-sulphonate with 3-substituted 5-iodonorbornane-2,6-lactones

“…C22H2205S requires C, 66.35; H, 5.55; S, 8.05%); v,,,,,. (CHCI,) I 734 (s, CO) and 1 598 cm" (m, aromatic); 6(90 MHz; CDCI,) 7 (2.4 g, 8.2 mmol) in anhydrous acetonitrile (20 nil) was added dropwise over 45 min to a well stirred solution of silver toluene-4-sulphondte (6.3 g, 23 mmol) in anhydrous acetonitrile (35 ml) cooled in an ice-bath to 5 "C and protected from light under nitrogen. After addition was complete, the ice-bath was removed and the temperature allowed to rise to room temperature over the next hour.…”

“…7.0. C15H1602 requires C, 78.95; H, 7.0%), 2400 (m, C02H), 1710 (s, CO), and 1600 cm-l (m, aromatic); 6(60 MHz; CDCl,) 11.50 (s, 9-H), 7.20 (m, Ph), 6.20 (m, 5-, 6-H), 2.98br (s, 4-H), 2.80 (m, 3-H, 2.60 (m, 1-H), 2.35 (dq, 8-H), 2.10 (m, 2-H), and 1.65 (m, 7-anti-, 7-syn-H); J (8a, 8b) 12 Hz; mle 228 ( M + ) , 151 (M+ -Ph), and 160 A solution of this acid (2.0 g, 9.77 mmol) in aqueous 0 .…”