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Cycloaddition of Trichloronitrosomethane to Conjugated Dienes
Author(s) -
Lin ChengTung,
Chen JyunHung
Publication year - 1987
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.198700048
Subject(s) - chemistry , cycloaddition , oxazines , conjugated system , adduct , hydrolysis , ether , medicinal chemistry , organic chemistry , catalysis , polymer
Addition of trichloronitrosomethane to 1,3‐cycloalkadienes gives [2+4] cpclo‐adducts. However, reactions with acyclic 1,3‐butadienes afford unstable cycloadducts which hydrolyze in water‐ether solution to produce N ‐chloroformyl‐3,6‐dihydro‐l, 2‐oxazines. The later compounds are reduced to N ‐methyl or converted to N ‐methoxylcarbonyl derivatives in high yields.
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