Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Report | Regular issue | Vol 19, No. 7, 1982, pp.1269-1275
Published online, 1st January, 1970
DOI: 10.3987/R-1982-07-1269
Selective Cleavage of Unsymmetrical 2,2-Spiro-1,3-dioxolanes. II. Cleavage of Ketal Ring of 5’-Bromo-6’,7’-dihydro-4-isopropylaminomethyl-1’-p-toluenesulfonyl-spiro[1,3-dioxolane-2,4’-(5H’)-indole and Its Analogs

Makiko Sakai

*Shionogi Research Laboratories, Shionogi & Co. Ltd., Fukushima-ku, Osaka 553-0002, Japan


The bromodioxolane and its analogs (1-5) were treated with organic base (DBU, DBN, or morpholine), acid (p-toluenesulfonic acid or Lewis acid), or Lewis acid/tertiary amine, and yielded 4-alkoxyindoles (6-17). Reaction of 1 with organic base gave two isomeric 4-alkoxyindoles, 6 (tosylpindolol, a secondary alcohol) and 11 (a primary alcohol), while tri-n-octylamine with stannic chloride afforded 6 (74 %) without producing 11.