76055-26-0Relevant academic research and scientific papers
Adducts from Quinones and Diazoalkanes. Part 9. The Adduct from 2-methyl-1,4-naphthoquinone and Diazoethane and the Derived Secondary Carbanion: Regioisomerism in Carbanion-Quinone Additions
Dean, Francis M.,Houghton, Leonard E.,Nayyir-Mashir, Rassoul,Thebtaranonth, Chachanat
, p. 1994 - 2000 (2007/10/02)
Diazoethane adds to 2-methyl-1,4-naphthoquinone giving mainly one regioisomeric pyrazoline (5a) as a mixture of epimers at position 3.The other regioisomer was detected and a related compound (7) was obtained from a similar reaction with diazomethane.The pyrazoline (5a) is transformed into the carbanion (3b) with base ans thence into the butylenequinone (9).Thermal decomposition affords 2-ethyl-3-methyl-1,4-naphthoquinone.Treatment with methanolic base and 2-methyl-1,4-naphthoquinone gives the fluorene derivative (11a) not the expected alcohol (12).Treatment with methanolic base and trimethyl-1,4-benzoquinone affords the expected xanthen derivative (16) but the congeneric fluorene alcohols differed regiospecifically from those observed in other series.One (14) has a cis-fused nucleus; the other is believed to be the trans-fused analogue (13), another departure from previous experience.On the other hand, the reaction with 2,5-dimethyl-1,4-benzoquionone leads to the cage tetraketone (17a) as expected.
