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Hydrated Oxocarbons, II. Preparation of a New Class of Thermochromic Boron Heterocycles from Octahydroxycyclobutane or Dihydroxybutenedioic Acid
Author(s) -
Yalpani Mohamed,
Köster Roland
Publication year - 1983
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19831161009
Subject(s) - chemistry , thermochromism , triethylborane , alkyl , aryl , solid state , medicinal chemistry , polymer chemistry , yield (engineering) , organic chemistry , catalysis , materials science , metallurgy
The reaction of octahydroxycyclobutane ( 2 ) with activated triethylborane gives a low yield of the thermochromic 2,6‐diethyl‐1,3,5,7‐tetraoxa‐2,6‐dibora‐4,8‐octalindione ( 5b ) by ring cleavage of 2 . Additional examples of this novel class of compounds have also been prepared directly by reacting dihydroxyfumaric acid ( 6 ) with various alkyl‐ or arylboranes. With the exception of the tert ‐butyl‐ ( 5f ) and the aryl derivatives 51 , m , the new compounds 5 undergo a temperature dependent colour change (yellow/colourless) in the solid state. The thermochromic transition temperature T th depends on the substituents and lies between −5 and 150°C.