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Synthesis and Properties of 7,7,12,12-Tetramethyl-1,4-dioxacyclotetradecane-8,9,10,11-tetrone

✍ Scribed by Christoph Braunweiler; Sabine Bethke; Frank Rominger; Rolf Gleiter

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 300 KB
Volume: 1999
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199906)1999:6<1303::aid-ejoc1303>3.0.co;2-m

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✦ Synopsis

The fourteen-membered ring of 7,7,12,12-tetramethyl-1,4-(R,S) isomer 18a revealed a transannular interaction between the dioxaethane bridge and the dicarbonyl moiety. dioxacyclotetradecane-8,9,10,11-tetrone (4) was built up from 1,2-bis(2Ј-chloroethoxy)ethane, two units derived from Calculations (HF/6-31G*) on 4 predict relatively short distances between the oxygen atoms of the dioxyethane isobutyric acid and acetylene. Key intermediates were 2,2,11,11-tetramethyl-5,8-dioxadodecane-1,12-diol (8), bridge and the (CO) 4 part. Investigations by means of cyclic voltammetry, PE and UV/Vis spectroscopy on 4 reveal an 7,7,12,12-tetramethyl-1,4-dioxa-9-cyclotetradecyne-2,8-diol protected by one tetrahydropyran group (15), and 8,11-interaction between the dioxaethane bridge and the (CO) 4 group. dihydroxy-7,7,12,12-tetramethyl-1,4-dioxacyclotetradecane-9,10-dione (18). X-ray investigation on single crystals of the

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