Direct formation of methylenecyclopentanes by cycloaddition of a

Jerome A. Berson, Dale M. McDaniel, Leonard R. Corwin, and James H. Davis. J. Am. Chem. Soc. , 1972, 94 (15), pp 5508–5509. DOI: 10.1021/ja00770a063...
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5508

Scheme I

Ph,+.,N Ph

N, ’Ph

-kP

nonconcerted 1,3-sigmatropic rearrangement (e.g., 3 + 5 + 4). Moreover, the cycloadditions are of potential importance in synthesis as a direct route to methylenecyclopentanes.

h - N H w & P h

Ph

5

4

X,

4 + 5 -

+

a

1

Ph N

N

w

6

N

,

p

+

h

TFA

-----*

7

H P

7(or8) 6

+

base

-

+

h

-

excessTFA

N

w

-

-N