User:Thenarganaut/sandbox

=Drafts=

Edward G. Budd Mfg. Co. v. National Labor R. Board, 138 F.2d 86 (3d Cir. 1943)
https://law.justia.com/cases/federal/appellate-courts/F2/138/86/1481608/

NLRB v. Gissel Packing Co., Inc., 395 U.S. 575 (1969)
NLRB v. Gissel Packing Co., Inc., 395 U.S. 575 was a United States Supreme Court case decided in 1969 clarifying the application of the National Labor Relations Act after the Taft-Hartley Amendments, particularly the application of union authorization cards.

Mechanism


The first step is a nucleophilic attack by the imine nitrogen on the carbonyl carbon to generate a zwitterionic intermediate. Electron donating groups on the imine facilitate this step, while electron-withdrawing groups impede the attack. The second step is a conrotary electrocyclic ring closure. The electrocyclic ring closure step is different from typical ring closures as predicted by the Woodward–Hoffmann rules. Under photochemical and microwave conditions the intermediate's 4π-electron system cannot undergo a disrotatory ring closure to form the β-lactam, possibly because the two double bonds are not coplanar. The above mechanism is the verified mechanism in solution. There is evidence from computational studies on model systems that in the gas phase the mechanism is concerted.

Stereochemistry
The stereochemistry of the Staudinger Synthesis can be difficult to predict because either step can be rate-determining. If the ring closure step is rate-determining, stereochemical predictions based on torquoselectivity are reliable. Other factors that affect the stereochemistry include the initial regiochemistry of the imine. Generally, (E)-imines form cis β-lactams while (Z)-imines form trans β-lactams. Other substituents affect the stereochemistry as well. Ketenes with strong electron-donating substituents mainly produce cis β-lactams, while ketenes with strong electron-withdrawing substituents generally produce trans β-lactams. The ketene substituent affects the transition state by either speeding up or slowing down the progress towards the β-lactam. A slower reaction allows for the isomerization of the imine, which generally results in a trans product.