3306-02-3Relevant articles and documents
Addition of dichloro- and dibromocarbene to 1,2-diphenylcyclobutene
Wagner, Robert A.,Weber, Juergen,Brinker, Udo H.
, p. 246 - 247 (2000)
1,2-Diphenylcyclobutene (7) was reacted with dibromo- and dichlorocarbene, both generated via three different methods. 1,3-Diphenyl-2-halocyclopenta-1,3-dienes 12 were isolated which result from addition of the dihalocarbenes to the cyclobutene double bond of 7. A cationic cyclopropyl-allyl rearrangement (CCA) in gem-dihalobicyclopentanes 8 leads to 2,3-dihalocyclopentenes 9, which under the reaction conditions are dehydrohalogenated to 12. A second carbene addition and rearrangement afford aromatic compounds 11 and 16.
Attempted preparation of 5,5-difluoro-1,4-diphenylbicyclo[2.1.0]pentane - Serendipitous synthesis of 1,3-difluoro-2,4-diphenylbenzene
Lewis,Borden
, p. 1357 - 1360 (1994)
Addition of difluorocarbene to 1,2-diphenylcyclobutene, using PhHgCF3, results in formation of 1,3-difluoro-2,4-diphenylbenzene. A mechanism for this reaction is proposed.
Stereoselective Synthesis of anti-1,4-Diols by a BH3· THF-Mediated Rearrangement of 1,2-Disubstituted Cyclobutenes
Knapp, Kolja M.,Goldfuss, Bernd,Knochel, Paul
, p. 5259 - 5265 (2007/10/03)
A new stereoselective rearrangement of cyclobutylboranes, obtained by the hydroboration of 1,2-disubstituted cyclobutenes, provides anti-1,4-diols with good-to-excellent diastereoselectivity. The mechanism of the rearrangement is discussed based on theoretical calculations.