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Synthesis and properties of 7,7,12,12-tetramethyl-1,4-dioxacyclotetradecane-8,9,10,11-tetrone

The fourteen-membered ring of 7,7,12,12-tetramethyl-1,4-dioxacyclotetradecane-8,9,10,11-tetrone (4) was built up from 1,2-bis(2?-chloroethoxy)ethane, two units derived from isobutyric acid and acetylene. Key intermediates were 2,2,11,11-tetramethyl-5,8-dioxadodecane-1,12-diol (8), 7,7,12,12-tetramet...

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Bibliographic Details
Main Authors: Braunweiler, Christoph (Author) , Bethke, Sabine (Author) , Rominger, Frank (Author) , Gleiter, Rolf (Author)
Format: Article (Journal) Festschrift
Language:English
Published: 12 May 1999
In: European journal of organic chemistry
Year: 1999, Issue: 6, Pages: 1303-1310
ISSN:1099-0690
DOI:10.1002/(SICI)1099-0690(199906)1999:6<1303::AID-EJOC1303>3.0.CO;2-M
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Festschrift
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/(SICI)1099-0690(199906)1999:6<1303::AID-EJOC1303>3.0.CO;2-M
Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/%28SICI%291099-0690%28199906%291999%3A6%3C1303%3A%3AAID-EJOC1303%3E3.0.CO%3B2-M
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Author Notes:Christoph Braunweiler, Sabine Bethke, Frank Rominger, and Rolf Gleiter
Description
Summary:The fourteen-membered ring of 7,7,12,12-tetramethyl-1,4-dioxacyclotetradecane-8,9,10,11-tetrone (4) was built up from 1,2-bis(2?-chloroethoxy)ethane, two units derived from isobutyric acid and acetylene. Key intermediates were 2,2,11,11-tetramethyl-5,8-dioxadodecane-1,12-diol (8), 7,7,12,12-tetramethyl-1,4-dioxa-9-cyclotetradecyne-2,8-diolprotected by one tetrahydropyran group (15), and 8,11-dihydroxy-7,7,12,12-tetramethyl-1,4-dioxacyclotetradecane-9,10-dione (18). X-ray investigation on single crystals of the (R,S) isomer 18a revealed a transannular interaction between the dioxaethane bridge and the dicarbonyl moiety. Calculations (HF/6-31G*) on 4 predict relatively short distances between the oxygen atoms of the dioxyethane bridge and the (CO)4 part. Investigations by means of cyclic voltammetry, PE and UV/Vis spectroscopy on 4 reveal an interaction between the dioxaethane bridge and the (CO)4 group.
Item Description:Dedicated to Professor Werner Tochtermann on the occasion of his 65th birthday
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Physical Description:Online Resource
ISSN:1099-0690
DOI:10.1002/(SICI)1099-0690(199906)1999:6<1303::AID-EJOC1303>3.0.CO;2-M

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