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medrings - 7-MEMBERED RING FORMATION Medium Sized Rings...

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7-MEMBERED RING FORMATION 168 Medium Sized Rings 7-Membered Rings [4+2] cycloadditions - [4+2] cycloadditions between dienes and allylcations leads to cycloheptadienes review: ACIEE 1984 , 23 , 1; ACIEE 1973 , 12 , 819 + + + I Me ACIEE 1973 , 12 , 819 ACIEE 1984 , 23 , 1 -78°C + CF 3 CO 2 Ag F 3 CCO 2 SiMe 3 SiMe 3 H H + ZnCl 2 , -30°C + ACIEE 1982 , 21 , 442 OTMS Br O ZnCl 2 O + JACS 1982 , 104 , 1330 O O O OMe O O O O O O O O O O HO + + mCPBA JACS 1979 , 101 , 226 - Noyori [4+2] cycloaddition of α , α '-dibromoketones and dienes review: ACR 1979 , 12 , 61 R R O Br Br R R OM R R O Fe 2 (CO) 9 -or- Zn-Cu + ACR 1979 , 61 Organic Reactions 1983 , 29 , 163
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7-MEMBERED RING FORMATION 169 Br Br O Br Br O Br Br O O O O Fe 2 (CO) 9 Zn Br Br O Br Br N CO 2 Me N O MeO 2 C 1) 2) Zn Fe 2 (CO) 9 JACS 1978 , 100 , 1786 Tetrahedron 1985 , 41 , 5879 O O O OMe O O O O O O O O O O HO + + mCPBA JACS 1979 , 101 , 226 Me Me O Br Br O O O O O O O OH CO 2 H H H 1) H2, Pd/C 2) CF 3 CO 3 H 1) Fe 2 (CO) 9 JACS 1972 , 94 , 3940 JOC 1976 , 41 , 2075 O O OBn O O O OBn O O OH Me OBn OH Me Me OH Me 1) CF 3 CO 3 H 2) LDA, MeI JCSCC 1985 , 55 - [4+2] cycloaddition between pentadienyl cations and olefins + + + O O HO O OH - O O O Δ + Tetrahedron 1966 ,
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