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3‐Methylenetricyclo[3.1.0.0 2,6 ]hexane, a Tricyclic Isomer of Toluene: Synthesis and Addition onto Tetracyanoethylene
Author(s) -
Hasselmann Dieter,
Loosen Klaus,
Fischer Thomas,
Kunz Ulrike,
Christl Manfred
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200204)2002:8<1374::aid-ejoc1374>3.0.co;2-s
Subject(s) - tetracyanoethylene , chemistry , toluene , hexane , derivative (finance) , contraction (grammar) , organic chemistry , ring (chemistry) , medicinal chemistry , stereochemistry , medicine , financial economics , economics
A multistep ring‐contraction route starting from tricyclo[4.1.0.0 2,7 ]heptan‐3‐one ( 1 ) resulted in a mixture of the title compound 7 and the homofulvene 8 in a ratio of 1:2.5. In a second synthesis, a 3.5:1 mixture of 7 and three additional hydrocarbons was obtained from 4‐(phenylsulfanyl)tricyclo[3.1.0.0 2,6 ]hexan‐3‐one ( 9 ) in a two‐step sequence. On being heated at 175 °C in solution, 7 rearranged to toluene. Treatment of 7 with tetracyanoethylene gave rise to a 1:5 mixture of the [2+2] cycloadduct 16 and the cyclopropadicyclopentene derivative 17 . (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)