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Mg° / Et2O
Alkyl halide to MgX.
Li° / Et2O
Alkyl halide to R-Li.
epoxide / 2. aq. HCl
LG substituted with opened epoxide (start with R-Li or R-MgX).
R-MgBr, Et2O / 2. HCl, H2O
(Open ring via less hindered), add R via SN2, cap O- with H.
R-Li, Et2O / 2. aq. HCl
(Open ring via less substituted), add R via SN2, cap O- with H.
CuI / Et2O
2 R-Li + CuI → R2CuLi (symmetrical, taken from R-Li).
R2CuLi / Et2O
Transfer 1 R (if starting with alkyl halide → halide leaves, 1 side of R2 attaches, 1° = SN2-like, 3 groups = retain stereochem).
KO-t-Bu / CHCl3
Double bond to 1,1-dichlorocyclopropane, check E/Z before.
CH2I2 / Zn(Cu), Et2O
Double bond to cyclopropane.