In:
Israel Journal of Chemistry, Wiley, Vol. 25, No. 1 ( 1985-01), p. 74-83
Abstract:
A new synthesis of cyclobutenedione (1) is described. It is found that the tricyclic cyclobutanedione 3 splits into 1 and cyclopentadiene if subjected to flash pyrolysis conditions. The dienophilic reactivity of 1 allows the construction of various polycyclic cyclobutanediones, such as 3–5 and 12–14. Other new polycyclic diones, like 9–11, 15 and 16 are prepared by means of the acyloin condensation. The low stereoselectivity of 1 with cyclopentadiene is compared with the selectivity of other cyclobutenes, and the results are placed in the context of secondary interactions and steric hindrance. The unusual colour properties of these diones, from colourless 1 to blue 6 are investigated by means of photoelectron spectroscopic measurements and semi‐empirical calculations (MNDO, HAM/3, CNDO/S‐CI).
Type of Medium:
Online Resource
ISSN:
0021-2148
,
1869-5868
DOI:
10.1002/ijch.198500013
Language:
English
Publisher:
Wiley
Publication Date:
1985
detail.hit.zdb_id:
2066481-3
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